| 2024-04-20 15:00:0020/04/2024 15:00 | Chesterfield | 15:00:0015:00 | Maidenhead | National League | N/A |
| 2024-04-13 15:00:0013/04/2024 15:00 | Wealdstone | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-04-06 15:00:0006/04/2024 15:00 | Gateshead | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-04-01 15:00:0001/04/2024 15:00 | Chesterfield | 15:00:0015:00 | Kidderminster | National League | N/A |
| 2024-03-29 15:00:0029/03/2024 15:00 | York | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-03-23 15:00:0023/03/2024 15:00 | Chesterfield | 15:00:0015:00 | Boreham W | National League | N/A |
| 2024-03-16 15:00:0016/03/2024 15:00 | Oldham | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-03-12 19:45:0012/03/2024 19:45 | Chesterfield | 19:45:0019:45 | Oxford City | National League | N/A |
| 2024-03-09 15:00:0009/03/2024 15:00 | Chesterfield | 15:00:0015:00 | AFC Fylde | National League | N/A |
| 2024-03-02 15:00:0002/03/2024 15:00 | Dorking | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-02-24 15:00:0024/02/2024 15:00 | Chesterfield | 15:00:0015:00 | Rochdale | National League | N/A |
| 2024-02-20 19:45:0020/02/2024 19:45 | Halifax | 19:45:0019:45 | Chesterfield | National League | N/A |
| 2024-02-17 15:00:0017/02/2024 15:00 | Bromley | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-02-10 15:00:0010/02/2024 15:00 | Chesterfield | 15:00:0015:00 | Ebbsfleet | National League | N/A |
| 2024-02-03 15:00:0003/02/2024 15:00 | Eastleigh | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-01-27 15:00:0027/01/2024 15:00 | Chesterfield | 15:00:0015:00 | Southend | National League | N/A |
| 2024-01-23 19:45:0023/01/2024 19:45 | Chesterfield | 19:45:0019:45 | Woking | National League | N/A |
| 2024-01-20 15:00:0020/01/2024 15:00 | Barnet | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-01-16 19:45:0016/01/2024 19:45 | Chesterfield | 19:45:0019:45 | Altrincham | National League | N/A |
| 2024-01-06 15:00:0006/01/2024 15:00 | Dagenham | 15:00:0015:00 | Chesterfield | National League | N/A |
| 2024-01-01 15:00:0001/01/2024 15:00 | Chesterfield | 3 - 2 | Solihull | National League | N/A |
| 2023-12-26 15:00:0026/12/2023 15:00 | Solihull | 2 - 0 | Chesterfield | National League | N/A |
| 2023-12-23 15:00:0023/12/2023 15:00 | Chesterfield | 4 - 1 | Aldershot | National League | N/A |
| 2023-12-16 15:00:0016/12/2023 15:00 | Hartlepool | 0 - 1 | Chesterfield | National League | N/A |
| 2023-12-09 15:00:0009/12/2023 15:00 | Chesterfield | 6 - 1 | Southport | FA Trophy | N/A |
| 2023-12-03 14:00:0003/12/2023 14:00 | Chesterfield | 1 - 0 | Leyton Orient | FA Cup | N/A |
| 2023-11-25 15:00:0025/11/2023 15:00 | Chesterfield | 3 - 2 | Eastleigh | National League | N/A |
| 2023-11-21 19:45:0021/11/2023 19:45 | Woking | 0 - 2 | Chesterfield | National League | N/A |
| 2023-11-18 15:00:0018/11/2023 15:00 | Southend | 2 - 1 | Chesterfield | National League | N/A |
| 2023-11-11 15:00:0011/11/2023 15:00 | Chesterfield | 4 - 2 | Barnet | National League | N/A |
| 2023-11-05 12:15:0005/11/2023 12:15 | Chesterfield | 1 - 0 | Portsmouth | FA Cup | N/A |
| 2023-10-28 15:00:0028/10/2023 15:00 | Kidderminster | 1 - 3 | Chesterfield | National League | N/A |
| 2023-10-24 19:45:0024/10/2023 19:45 | Chesterfield | 4 - 0 | York | National League | N/A |
| 2023-10-21 15:00:0021/10/2023 15:00 | Chesterfield | 15:00:00Postponed | Gateshead | National League | N/A |
| 2023-10-14 15:00:0014/10/2023 15:00 | Chesterfield | 5 - 0 | Kettering | FA Cup | N/A |
| 2023-10-07 15:00:0007/10/2023 15:00 | Boreham W | 0 - 2 | Chesterfield | National League | N/A |
| 2023-10-03 19:45:0003/10/2023 19:45 | Chesterfield | 2 - 0 | Bromley | National League | N/A |
| 2023-09-30 15:00:0030/09/2023 15:00 | Maidenhead | 1 - 1 | Chesterfield | National League | N/A |
| 2023-09-26 20:00:0026/09/2023 20:00 | Rochdale | 1 - 2 | Chesterfield | National League | N/A |
| 2023-09-23 15:00:0023/09/2023 15:00 | Chesterfield | 3 - 2 | Wealdstone | National League | N/A |
| 2023-09-19 19:45:0019/09/2023 19:45 | Chesterfield | 3 - 2 | Halifax | National League | N/A |
| 2023-09-16 15:00:0016/09/2023 15:00 | Ebbsfleet | 0 - 1 | Chesterfield | National League | N/A |
| 2023-09-09 15:00:0009/09/2023 15:00 | Chesterfield | 3 - 1 | Dagenham | National League | N/A |
| 2023-09-02 15:00:0002/09/2023 15:00 | Aldershot | 3 - 4 | Chesterfield | National League | N/A |
| 2023-08-28 15:00:0028/08/2023 15:00 | Chesterfield | 3 - 2 | Hartlepool | National League | N/A |
| 2023-08-26 15:00:0026/08/2023 15:00 | Altrincham | 2 - 1 | Chesterfield | National League | N/A |
| 2023-08-19 12:30:0019/08/2023 12:30 | Chesterfield | 1 - 1 | Oldham | National League | N/A |
| 2023-08-15 19:45:0015/08/2023 19:45 | Oxford City | 1 - 2 | Chesterfield | National League | N/A |
| 2023-08-12 15:00:0012/08/2023 15:00 | AFC Fylde | 2 - 4 | Chesterfield | National League | N/A |
| 2023-08-05 15:00:0005/08/2023 15:00 | Chesterfield | 4 - 3 | Dorking | National League | N/A |
| 2023-08-01 19:45:0801/08/2023 19:45 | Basford | 3 - 0 | Chesterfield | Club Friendly | N/A |
| 2023-07-29 13:00:0029/07/2023 13:00 | Bris Rovers | 2 - 0 | Chesterfield | Club Friendly | N/A |
| 2023-07-22 15:00:0022/07/2023 15:00 | Accrington | 2 - 3 | Chesterfield | Club Friendly | N/A |
| 2023-07-19 19:00:0019/07/2023 19:00 | Chesterfield | 0 - 1 | Derby | Club Friendly | N/A |
| 2023-07-15 15:00:0015/07/2023 15:00 | Chesterfield | 0 - 2 | Sheff United | Club Friendly | N/A |
| 2023-07-11 19:00:0011/07/2023 19:00 | Chesterfield | 1 - 2 | Sheff Wed | Club Friendly | N/A |
| 2023-07-08 15:00:0408/07/2023 15:00 | Alfreton | 1 - 5 | Chesterfield | Club Friendly | N/A |
| 2023-07-04 19:45:0004/07/2023 19:45 | Matlock | 0 - 9 | Chesterfield | Club Friendly | N/A |
| 2023-05-13 15:30:0013/05/2023 15:30 | Chesterfield | 2 (3) - 2 (4) | Notts County | National League Playoffs | N/A |
| 2023-05-07 15:30:4907/05/2023 15:30 | Chesterfield | 3 - 2 | Bromley | National League Playoffs | N/A |
| 2023-04-29 17:30:0029/04/2023 17:30 | Chesterfield | 4 - 0 | Maidstone | National League | N/A |
| 2023-04-22 15:00:0022/04/2023 15:00 | Bromley | 2 - 0 | Chesterfield | National League | N/A |
| 2023-04-18 19:45:0018/04/2023 19:45 | Chesterfield | 5 - 1 | Torquay | National League | N/A |
| 2023-04-15 15:00:0015/04/2023 15:00 | Chesterfield | 3 - 2 | Eastleigh | National League | N/A |
| 2023-04-10 15:00:0010/04/2023 15:00 | Dagenham | 0 - 1 | Chesterfield | National League | N/A |
| 2023-04-07 15:00:0007/04/2023 15:00 | Chesterfield | 1 - 3 | York | National League | N/A |
| 2023-04-01 15:00:0001/04/2023 15:00 | Maidenhead | 0 - 0 | Chesterfield | National League | N/A |
| 2023-03-25 15:00:0025/03/2023 15:00 | Chesterfield | 2 - 0 | Halifax | National League | N/A |
| 2023-03-18 12:30:0018/03/2023 12:30 | Woking | 0 - 1 | Chesterfield | National League | N/A |
| 2023-03-14 19:45:0014/03/2023 19:45 | Wealdstone | 0 - 4 | Chesterfield | National League | N/A |
| 2023-03-11 15:00:0011/03/2023 15:00 | Chesterfield | 1 - 1 | Yeovil | National League | N/A |
| 2023-03-07 19:45:0007/03/2023 19:45 | Southend | 1 - 2 | Chesterfield | National League | N/A |
| 2023-03-04 15:00:0004/03/2023 15:00 | Gateshead | 1 - 2 | Chesterfield | National League | N/A |
| 2023-02-28 19:45:0028/02/2023 19:45 | Wrexham | 2 - 1 | Chesterfield | National League | N/A |
| 2023-02-25 15:00:0025/02/2023 15:00 | Chesterfield | 0 - 1 | Oldham | National League | N/A |
| 2023-02-21 19:45:0021/02/2023 19:45 | Chesterfield | 1 - 1 | Wealdstone | National League | N/A |
| 2023-02-18 15:00:0018/02/2023 15:00 | Solihull | 0 - 0 | Chesterfield | National League | N/A |
| 2023-02-14 19:45:0014/02/2023 19:45 | Aldershot | 1 - 1 | Chesterfield | National League | N/A |
| 2023-02-11 17:20:0011/02/2023 17:20 | Chesterfield | 1 - 2 | Notts County | National League | N/A |
| 2023-02-07 19:45:0007/02/2023 19:45 | Chesterfield | 1 - 3 | Woking | National League | N/A |
| 2023-02-04 15:00:0004/02/2023 15:00 | Boreham W | 1 - 0 | Chesterfield | National League | N/A |
| 2023-01-28 15:00:0028/01/2023 15:00 | Barnet | 3 - 0 | Chesterfield | National League | N/A |
| 2023-01-24 19:45:0024/01/2023 19:45 | Chesterfield | 1 - 0 | Altrincham | National League | N/A |
| 2023-01-17 20:00:0017/01/2023 20:00 | West Brom | 4 - 0 | Chesterfield | FA Cup | N/A |
| 2023-01-07 15:00:0007/01/2023 15:00 | Chesterfield | 3 - 3 | West Brom | FA Cup | N/A |
| 2023-01-01 15:00:0001/01/2023 15:00 | Chesterfield | 4 - 1 | Scunthorpe | National League | N/A |
| 2022-12-26 15:00:0026/12/2022 15:00 | Scunthorpe | 1 - 2 | Chesterfield | National League | N/A |
| 2022-12-20 19:45:0020/12/2022 19:45 | Chesterfield | 1 - 3 | Coalville | FA Trophy | N/A |
| 2022-12-10 15:00:0010/12/2022 15:00 | Chesterfield | 3 - 1 | Dorking | National League | N/A |
| 2022-12-03 12:30:0003/12/2022 12:30 | Halifax | 1 - 0 | Chesterfield | National League | N/A |
| 2022-11-26 15:00:0026/11/2022 15:00 | Wimbledon | 0 - 2 | Chesterfield | FA Cup | N/A |
| 2022-11-19 15:00:0019/11/2022 15:00 | Chesterfield | 2 - 0 | Solihull | National League | N/A |
| 2022-11-12 15:00:0012/11/2022 15:00 | Torquay | 1 - 5 | Chesterfield | National League | N/A |
| 2022-11-05 15:00:0005/11/2022 15:00 | Chesterfield | 1 - 0 | Northampton | FA Cup | N/A |
| 2022-11-01 19:45:0001/11/2022 19:45 | Chesterfield | 2 - 1 | Gateshead | National League | N/A |
| 2022-10-29 15:00:0029/10/2022 15:00 | Chesterfield | 2 - 0 | Boreham W | National League | N/A |
| 2022-10-25 19:45:0025/10/2022 19:45 | York | 1 - 1 | Chesterfield | National League | N/A |
| 2022-10-22 15:00:0022/10/2022 15:00 | Chesterfield | 3 - 2 | Bromley | National League | N/A |
| 2022-10-15 12:30:0015/10/2022 12:30 | Anstey Nomads | 0 - 3 | Chesterfield | FA Cup | N/A |
| 2022-10-08 15:00:0008/10/2022 15:00 | Eastleigh | 2 - 1 | Chesterfield | National League | N/A |
| 2022-10-04 19:45:0004/10/2022 19:45 | Chesterfield | 2 - 3 | Dagenham | National League | N/A |
| 2022-10-01 15:00:0001/10/2022 15:00 | Chesterfield | 1 - 2 | Maidenhead | National League | N/A |
| 2022-09-24 15:00:0024/09/2022 15:00 | Maidstone | 1 - 2 | Chesterfield | National League | N/A |
| 2022-09-17 15:00:0017/09/2022 15:00 | Yeovil | 2 - 2 | Chesterfield | National League | N/A |
| 2022-09-13 19:45:0013/09/2022 19:45 | Chesterfield | 3 - 2 | Southend | National League | N/A |
| 2022-09-03 15:00:0003/09/2022 15:00 | Oldham | 0 - 2 | Chesterfield | National League | N/A |
| 2022-08-29 15:00:0029/08/2022 15:00 | Altrincham | 1 - 2 | Chesterfield | National League | N/A |
| 2022-08-26 19:45:0026/08/2022 19:45 | Chesterfield | 3 - 1 | Barnet | National League | N/A |
| 2022-08-20 17:20:0020/08/2022 17:20 | Notts County | 2 - 2 | Chesterfield | National League | N/A |
| 2022-08-16 19:45:0016/08/2022 19:45 | Chesterfield | 2 - 0 | Wrexham | National League | N/A |
| 2022-08-13 15:00:0013/08/2022 15:00 | Chesterfield | 1 - 0 | Aldershot | National League | N/A |
| 2022-08-06 15:00:0006/08/2022 15:00 | Dorking | 2 - 2 | Chesterfield | National League | N/A |
| 2022-07-29 19:00:3529/07/2022 19:00 | Boston | 0 - 2 | Chesterfield | Club Friendly | N/A |
| 2022-07-23 15:00:0023/07/2022 15:00 | Chesterfield | 3 - 0 | Bradford | Club Friendly | N/A |
| 2022-07-16 15:00:0016/07/2022 15:00 | Matlock | 0 - 2 | Chesterfield | Club Friendly | N/A |
| 2022-05-29 12:30:0629/05/2022 12:30 | Solihull | 3 - 1 | Chesterfield | National League Playoffs | N/A |
| 2022-05-24 19:45:1124/05/2022 19:45 | Halifax | 1 - 2 | Chesterfield | National League Playoffs | N/A |
| 2022-05-15 15:00:0015/05/2022 15:00 | Chesterfield | 0 - 0 | Woking | National League | N/A |
| 2022-05-07 12:30:0007/05/2022 12:30 | Torquay | 2 - 0 | Chesterfield | National League | N/A |
| 2022-05-02 15:00:0002/05/2022 15:00 | Chesterfield | 0 - 1 | Stockport | National League | N/A |
| 2022-04-30 15:00:0030/04/2022 15:00 | Bromley | 4 - 2 | Chesterfield | National League | N/A |
| 2022-04-23 15:00:0023/04/2022 15:00 | Chesterfield | 3 - 2 | Dover | National League | N/A |
| 2022-04-18 17:20:0018/04/2022 17:20 | Halifax | 2 - 0 | Chesterfield | National League | N/A |
| 2022-04-09 15:00:0009/04/2022 15:00 | Wealdstone | 1 - 2 | Chesterfield | National League | N/A |
| 2022-04-02 15:00:0002/04/2022 15:00 | Chesterfield | 1 - 4 | Grimsby | National League | N/A |
| 2022-03-26 15:00:0026/03/2022 15:00 | Notts County | 1 - 1 | Chesterfield | National League | N/A |
| 2022-03-22 19:45:0022/03/2022 19:45 | Altrincham | 1 - 0 | Chesterfield | National League | N/A |
| 2022-03-19 15:00:0019/03/2022 15:00 | Chesterfield | 1 - 0 | Maidenhead | National League | N/A |
| 2022-03-12 17:20:0012/03/2022 17:20 | Boreham W | 1 - 1 | Chesterfield | National League | N/A |
| 2022-03-05 15:00:0005/03/2022 15:00 | Chesterfield | 2 - 2 | Southend | National League | N/A |
| 2022-03-01 19:45:0001/03/2022 19:45 | Chesterfield | 3 - 1 | Notts County | National League | N/A |
| 2022-02-26 17:20:0026/02/2022 17:20 | Chesterfield | 1 - 0 | Yeovil | National League | N/A |
| 2022-02-22 19:45:0022/02/2022 19:45 | Chesterfield | 0 - 2 | Wrexham | National League | N/A |
| 2022-02-19 15:00:0019/02/2022 15:00 | Chesterfield | 2 - 3 | Solihull | National League | N/A |
| 2022-02-12 15:00:0012/02/2022 15:00 | Weymouth | 1 - 1 | Chesterfield | National League | N/A |
| 2022-02-08 19:45:0008/02/2022 19:45 | Stockport | 2 - 2 | Chesterfield | National League | N/A |
| 2022-02-05 15:00:0005/02/2022 15:00 | Chesterfield | 2 - 1 | Dagenham | National League | N/A |
| 2022-01-29 17:20:0029/01/2022 17:20 | Eastleigh | 0 - 1 | Chesterfield | National League | N/A |
| 2022-01-22 15:00:0022/01/2022 15:00 | Chesterfield | 0 - 0 | Aldershot | National League | N/A |
| 2022-01-18 19:45:0018/01/2022 19:45 | Maidenhead | 3 - 2 | Chesterfield | National League | N/A |
| 2022-01-15 15:00:0015/01/2022 15:00 | Barnet | 1 - 4 | Chesterfield | National League | N/A |
| 2022-01-08 17:30:0008/01/2022 17:30 | Chelsea | 5 - 1 | Chesterfield | FA Cup | N/A |
| 2022-01-01 15:00:0001/01/2022 15:00 | Chesterfield | 1 - 0 | King’s Lynn | National League | N/A |
| 2021-12-28 15:00:0028/12/2021 15:00 | Chesterfield | 1 - 1 | Halifax | National League | N/A |
| 2021-12-11 15:00:0011/12/2021 15:00 | Grimsby | 0 - 1 | Chesterfield | National League | N/A |
| 2021-12-05 17:15:0005/12/2021 17:15 | Salford | 0 - 2 | Chesterfield | FA Cup | N/A |
| 2021-11-23 19:45:0023/11/2021 19:45 | Chesterfield | 2 - 2 | Altrincham | National League | N/A |
| 2021-11-20 15:00:0020/11/2021 15:00 | Solihull | 0 - 2 | Chesterfield | National League | N/A |
| 2021-11-13 15:00:0013/11/2021 15:00 | Chesterfield | 4 - 0 | Weymouth | National League | N/A |
| 2021-11-06 15:00:0006/11/2021 15:00 | Chesterfield | 3 - 1 | Southend | FA Cup | N/A |
| 2021-10-30 15:00:0030/10/2021 15:00 | Dagenham | 2 - 2 | Chesterfield | National League | N/A |
| 2021-10-26 19:45:0026/10/2021 19:45 | Chesterfield | 1 - 0 | Eastleigh | National League | N/A |
| 2021-10-23 15:00:0023/10/2021 15:00 | Chesterfield | 2 - 1 | Boreham W | National League | N/A |
| 2021-10-16 15:00:0016/10/2021 15:00 | Curzon Ashton | 0 - 4 | Chesterfield | FA Cup | N/A |
| 2021-10-09 15:00:0009/10/2021 15:00 | Southend | 0 - 4 | Chesterfield | National League | N/A |
| 2021-10-05 19:45:0005/10/2021 19:45 | Wrexham | 1 - 1 | Chesterfield | National League | N/A |
| 2021-09-28 19:45:0028/09/2021 19:45 | Woking | 3 - 1 | Chesterfield | National League | N/A |
| 2021-09-25 17:20:0025/09/2021 17:20 | Chesterfield | 2 - 2 | Torquay | National League | N/A |
| 2021-09-18 15:00:0018/09/2021 15:00 | Yeovil | 0 - 2 | Chesterfield | National League | N/A |
| 2021-09-14 19:45:0014/09/2021 19:45 | Chesterfield | 4 - 2 | Barnet | National League | N/A |
| 2021-09-11 15:00:0011/09/2021 15:00 | Dover | 0 - 0 | Chesterfield | National League | N/A |
| 2021-09-04 15:00:0004/09/2021 15:00 | Chesterfield | 2 - 2 | Bromley | National League | N/A |
| 2021-08-30 15:00:0030/08/2021 15:00 | King’s Lynn | 0 - 2 | Chesterfield | National League | N/A |
| 2021-08-28 15:00:0028/08/2021 15:00 | Chesterfield | 2 - 0 | Wealdstone | National League | N/A |
| 2021-08-21 15:00:0021/08/2021 15:00 | Aldershot | 0 - 2 | Chesterfield | National League | N/A |
| 2021-08-14 14:00:0014/08/2021 14:00 | Chesterfield | 2 - 1 | Grimsby | Club Friendly | N/A |
| 2021-08-07 15:00:5807/08/2021 15:00 | Tamworth | 1 - 3 | Chesterfield | Club Friendly | N/A |
| 2021-07-31 15:00:1831/07/2021 15:00 | Chesterfield | 0 - 1 | Port Vale | Club Friendly | N/A |
| 2021-07-21 19:30:0021/07/2021 19:30 | Matlock | 1 - 3 | Chesterfield | Club Friendly | N/A |
| 2021-07-17 15:00:1217/07/2021 15:00 | Alfreton | 3 - 2 | Chesterfield | Club Friendly | N/A |
| 2021-06-05 16:00:4705/06/2021 16:00 | Notts County | 3 - 2 | Chesterfield | National League Playoffs | N/A |
| 2021-05-29 12:30:0029/05/2021 12:30 | Halifax | 1 - 2 | Chesterfield | National League | N/A |
| 2021-05-22 15:00:0022/05/2021 15:00 | Chesterfield | 2 - 1 | Dagenham | National League | N/A |
| 2021-05-15 15:00:0015/05/2021 15:00 | Chesterfield | 0 - 0 | Wealdstone | National League | N/A |
| 2021-05-11 19:45:0011/05/2021 19:45 | Chesterfield | 4 - 1 | King’s Lynn | National League | N/A |
| 2021-05-08 15:00:0008/05/2021 15:00 | Woking | 1 - 4 | Chesterfield | National League | N/A |
| 2021-05-03 15:00:0003/05/2021 15:00 | Chesterfield | 0 - 2 | Torquay | National League | N/A |
| 2021-05-01 17:20:0001/05/2021 17:20 | Hartlepool | 3 - 1 | Chesterfield | National League | N/A |
| 2021-04-27 19:45:0027/04/2021 19:45 | Bromley | 1 - 2 | Chesterfield | National League | N/A |
| 2021-04-24 15:00:0024/04/2021 15:00 | Wrexham | 0 - 0 | Chesterfield | National League | N/A |
| 2021-04-20 19:45:0020/04/2021 19:45 | Chesterfield | 1 - 2 | Halifax | National League | N/A |
| 2021-04-17 12:30:0017/04/2021 12:30 | Chesterfield | 1 - 2 | Bromley | National League | N/A |
| 2021-04-13 19:45:0013/04/2021 19:45 | Chesterfield | 0 - 0 | Boreham W | National League | N/A |
| 2021-04-10 15:00:0010/04/2021 15:00 | King’s Lynn | 1 - 2 | Chesterfield | National League | N/A |
| 2021-04-02 15:00:0002/04/2021 15:00 | Eastleigh | 0 - 1 | Chesterfield | National League | N/A |
| 2021-03-27 15:00:0027/03/2021 15:00 | Chesterfield | 1 - 0 | Weymouth | National League | N/A |
| 2021-03-23 19:00:0023/03/2021 19:00 | Aldershot | 0 - 1 | Chesterfield | National League | N/A |
| 2021-03-20 15:00:0020/03/2021 15:00 | Barnet | 0 - 2 | Chesterfield | National League | N/A |
| 2021-03-16 19:00:0016/03/2021 19:00 | Chesterfield | 0 - 1 | Sutton | National League | N/A |
| 2021-03-13 15:00:0013/03/2021 15:00 | Maidenhead | 2 - 0 | Chesterfield | National League | N/A |
| 2021-03-06 15:00:0006/03/2021 15:00 | Chesterfield | 3 - 0 | Yeovil | National League | N/A |
| 2021-03-02 19:45:0002/03/2021 19:45 | Chesterfield | 1 - 0 | Eastleigh | National League | N/A |
| 2021-02-27 15:00:0027/02/2021 15:00 | Stockport | 2 - 0 | Chesterfield | National League | N/A |
| 2021-02-23 19:45:0023/02/2021 19:45 | Chesterfield | 1 - 0 | Altrincham | National League | N/A |
| 2021-02-20 15:00:0020/02/2021 15:00 | Notts County | 0 - 1 | Chesterfield | National League | N/A |
| 2021-01-30 15:00:0030/01/2021 15:00 | Dagenham | 2 - 2 | Chesterfield | National League | N/A |
| 2021-01-26 19:45:0026/01/2021 19:45 | Boreham W | 0 - 0 | Chesterfield | National League | N/A |
| 2021-01-23 15:00:0023/01/2021 15:00 | Chesterfield | 2 - 1 | Wrexham | National League | N/A |
| 2021-01-20 19:45:0020/01/2021 19:45 | Boston | 1 (1) - 1 (4) | Chesterfield | FA Trophy | N/A |
| 2021-01-05 19:45:0005/01/2021 19:45 | Solihull | 2 - 1 | Chesterfield | National League | N/A |
| 2021-01-02 15:00:0002/01/2021 15:00 | Chesterfield | 1 - 0 | Solihull | National League | N/A |
| 2020-12-19 15:00:0019/12/2020 15:00 | Chesterfield | 0 (4) - 0 (3) | Brackley | FA Trophy | N/A |
| 2020-12-12 15:00:0012/12/2020 15:00 | Chesterfield | 6 - 0 | Barnet | National League | N/A |
| 2020-12-08 19:00:0008/12/2020 19:00 | Sutton | 0 - 1 | Chesterfield | National League | N/A |
| 2020-12-01 19:00:0001/12/2020 19:00 | Chesterfield | 0 - 0 | Aldershot | National League | N/A |
| 2020-11-28 15:00:0028/11/2020 15:00 | Weymouth | 1 - 2 | Chesterfield | National League | N/A |
| 2020-11-21 15:00:0021/11/2020 15:00 | Chesterfield | 2 - 3 | Notts County | National League | N/A |
| 2020-11-17 19:45:0017/11/2020 19:45 | Altrincham | 3 - 2 | Chesterfield | National League | N/A |
| 2020-11-14 15:00:0014/11/2020 15:00 | Chesterfield | 1 - 2 | Maidenhead | National League | N/A |
| 2020-11-04 19:45:0004/11/2020 19:45 | Stockport | 4 - 0 | Chesterfield | FA Cup | N/A |
| 2020-10-31 15:00:0031/10/2020 15:00 | Yeovil | 0 - 1 | Chesterfield | National League | N/A |
| 2020-10-20 19:45:0020/10/2020 19:45 | Wealdstone | 3 - 2 | Chesterfield | National League | N/A |
| 2020-10-17 17:20:0017/10/2020 17:20 | Chesterfield | 1 - 2 | Stockport | National League | N/A |
| 2020-10-13 19:45:0013/10/2020 19:45 | Torquay | 2 - 1 | Chesterfield | National League | N/A |
| 2020-10-10 15:00:0010/10/2020 15:00 | Chesterfield | 4 - 0 | Woking | National League | N/A |
| 2020-10-06 19:45:0006/10/2020 19:45 | Chesterfield | 1 - 2 | Hartlepool | National League | N/A |
| 2020-09-26 12:00:0026/09/2020 12:00 | Chesterfield | 0 - 1 | Guiseley | Club Friendly | N/A |
| 2020-09-19 12:00:0019/09/2020 12:00 | Alfreton | 2 - 0 | Chesterfield | Club Friendly | N/A |
| 2020-09-08 19:30:0008/09/2020 19:30 | Belper Town | 2 - 3 | Chesterfield | Club Friendly | N/A |
| 2020-03-14 15:00:0014/03/2020 15:00 | Dover | 1 - 1 | Chesterfield | National League | N/A |
| 2020-03-07 15:00:0007/03/2020 15:00 | Chorley | 1 - 2 | Chesterfield | National League | N/A |
| 2020-03-03 19:45:0003/03/2020 19:45 | Chesterfield | 3 - 4 | Harrogate | National League | N/A |
| 2020-02-22 15:00:0022/02/2020 15:00 | Chesterfield | 4 - 0 | Ebbsfleet | National League | N/A |
| 2020-02-08 13:00:0008/02/2020 13:00 | Chesterfield | 3 - 2 | Wrexham | National League | N/A |
| 2020-02-01 17:20:0001/02/2020 17:20 | Notts County | 3 - 0 | Chesterfield | National League | N/A |
| 2020-01-25 15:00:0025/01/2020 15:00 | Chesterfield | 1 - 1 | AFC Fylde | National League | N/A |
| 2020-01-18 15:00:0018/01/2020 15:00 | Eastleigh | 0 - 2 | Chesterfield | National League | N/A |
| 2020-01-04 15:00:0004/01/2020 15:00 | Chesterfield | 1 - 0 | Sutton | National League | N/A |
| 2020-01-01 15:00:0001/01/2020 15:00 | Solihull | 3 - 0 | Chesterfield | National League | N/A |
| 2019-12-28 15:00:0028/12/2019 15:00 | Halifax | 1 - 0 | Chesterfield | National League | N/A |
| 2019-12-26 15:00:0026/12/2019 15:00 | Chesterfield | 2 - 2 | Solihull | National League | N/A |
| 2019-12-21 15:00:0021/12/2019 15:00 | Torquay | 0 - 3 | Chesterfield | National League | N/A |
| 2019-12-14 13:00:0014/12/2019 13:00 | Chesterfield | 0 - 1 | Notts County | FA Trophy | N/A |
| 2019-12-10 19:45:0010/12/2019 19:45 | Chesterfield | 1 - 2 | Yeovil | National League | N/A |
| 2019-12-07 15:00:0007/12/2019 15:00 | Chesterfield | 1 - 2 | Bromley | National League | N/A |
| 2019-11-30 15:00:0030/11/2019 15:00 | Aldershot | 2 - 2 | Chesterfield | National League | N/A |
| 2019-11-26 19:45:0026/11/2019 19:45 | Chesterfield | 1 - 5 | Hartlepool | National League | N/A |
| 2019-11-23 15:00:0023/11/2019 15:00 | Harrogate | 3 - 1 | Chesterfield | National League | N/A |
| 2019-11-16 15:00:0016/11/2019 15:00 | Chesterfield | 2 - 3 | Chorley | National League | N/A |
| 2019-11-02 15:00:0002/11/2019 15:00 | Ebbsfleet | 2 - 2 | Chesterfield | National League | N/A |
| 2019-10-26 17:20:0026/10/2019 17:20 | Chesterfield | 1 - 0 | Notts County | National League | N/A |
| 2019-10-22 19:45:0022/10/2019 19:45 | Wrexham | 1 - 0 | Chesterfield | FA Cup | N/A |
| 2019-10-19 13:00:0019/10/2019 13:00 | Chesterfield | 1 - 1 | Wrexham | FA Cup | N/A |
| 2019-10-15 19:45:0015/10/2019 19:45 | Wrexham | 0 - 1 | Chesterfield | National League | N/A |
| 2019-10-08 19:45:0008/10/2019 19:45 | AFC Fylde | 1 - 3 | Chesterfield | National League | N/A |
| 2019-10-05 15:00:0005/10/2019 15:00 | Chesterfield | 1 - 2 | Eastleigh | National League | N/A |
| 2019-09-28 15:00:0028/09/2019 15:00 | Chesterfield | 2 - 1 | Aldershot | National League | N/A |
| 2019-09-24 19:45:0024/09/2019 19:45 | Hartlepool | 1 - 1 | Chesterfield | National League | N/A |
| 2019-09-21 15:00:0021/09/2019 15:00 | Sutton | 4 - 0 | Chesterfield | National League | N/A |
| 2019-09-14 15:00:0014/09/2019 15:00 | Chesterfield | 1 - 0 | Torquay | National League | N/A |
| 2019-09-07 15:00:0007/09/2019 15:00 | Bromley | 2 - 1 | Chesterfield | National League | N/A |
| 2019-09-03 19:45:0003/09/2019 19:45 | Chesterfield | 2 - 3 | Halifax | National League | N/A |
| 2019-08-31 15:00:0031/08/2019 15:00 | Chesterfield | 1 - 1 | Dagenham | National League | N/A |
| 2019-08-26 15:00:0026/08/2019 15:00 | Stockport | 2 - 0 | Chesterfield | National League | N/A |
| 2019-08-24 15:00:0024/08/2019 15:00 | Chesterfield | 2 - 2 | Barrow | National League | N/A |
| 2019-08-17 15:00:0017/08/2019 15:00 | Barnet | 2 - 2 | Chesterfield | National League | N/A |
| 2019-08-13 19:45:0013/08/2019 19:45 | Chesterfield | 1 - 2 | Woking | National League | N/A |
| 2019-08-10 15:00:0010/08/2019 15:00 | Boreham W | 2 - 2 | Chesterfield | National League | N/A |
| 2019-08-06 19:45:0006/08/2019 19:45 | Maidenhead | 1 - 1 | Chesterfield | National League | N/A |
| 2019-08-03 15:00:0003/08/2019 15:00 | Chesterfield | 1 - 2 | Dover | National League | N/A |
| 2019-07-27 15:00:0027/07/2019 15:00 | Chesterfield | 2 - 5 | Burton | Club Friendly | N/A |
| 2019-07-24 19:30:0024/07/2019 19:30 | Sheffield FC | 2 - 1 | Chesterfield | Club Friendly | N/A |
| 2019-07-23 19:30:0023/07/2019 19:30 | Chesterfield | 0 - 5 | Sheff United | Club Friendly | N/A |
| 2019-07-20 15:00:0020/07/2019 15:00 | Chesterfield | 1 - 2 | Rotherham | Club Friendly | N/A |
| 2019-07-16 19:30:0016/07/2019 19:30 | Matlock | 1 - 2 | Chesterfield | Club Friendly | N/A |
| 2019-07-15 19:30:0015/07/2019 19:30 | Hallam | 1 - 2 | Chesterfield | Club Friendly | N/A |
| 2019-07-13 15:00:0013/07/2019 15:00 | Staveley Miners | 4 - 4 | Chesterfield | Club Friendly | N/A |
| 2018-12-02 14:00:0002/12/2018 14:00 | Chesterfield | 0 - 2 | Grimsby | FA Cup | N/A |
| 2018-11-10 15:00:0010/11/2018 15:00 | Chesterfield | 1 - 1 | Billericay | FA Cup | N/A |
| 2018-07-25 19:00:5625/07/2018 19:00 | Chesterfield | 1 - 1 | Wigan | Club Friendly | N/A |
| 2018-07-07 12:00:4307/07/2018 12:00 | Sheffield FC | 1 - 5 | Chesterfield | Club Friendly | N/A |
