| Tuesday 1 May 2001 |
| Nationwide Division Three |
| Brighton |
1 (0) |
Chesterfield |
0 (0) |
| Saturday 28 April 2001 |
| Nationwide Division Three |
| Hull |
3 (2) |
Chesterfield |
1 (1) |
| Monday 16 April 2001 |
| Nationwide Division Three |
| Cardiff |
3 (1) |
Chesterfield |
3 (2) |
| Saturday 7 April 2001 |
| Nationwide Division Three |
| Leyton Orient |
2 (0) |
Chesterfield |
0 (0) |
| Saturday 10 March 2001 |
| Nationwide Division Three |
| Plymouth |
3 (1) |
Chesterfield |
0 (0) |
| Saturday 3 March 2001 |
| Nationwide Division Three |
| Macclesfield |
1 (1) |
Chesterfield |
2 (1) |
| Saturday 17 February 2001 |
| Nationwide Division Three |
| Mansfield |
0 (0) |
Chesterfield |
1 (1) |
| Tuesday 13 February 2001 |
| LDV Vans Trophy Northern Section - Semi Final |
| Lincoln City |
4 (1) |
Chesterfield |
1 (0) |
| Saturday 3 February 2001 |
| Nationwide Division Three |
| Barnet |
1 (0) |
Chesterfield |
1 (1) |
| Tuesday 30 January 2001 |
| LDV Vans Trophy Northern Section - Quarter Final |
| Bury |
0 (0) |
Chesterfield |
3 (3) |
| Tuesday 23 January 2001 |
| Nationwide Division Three |
| York |
0 (0) |
Chesterfield |
1 (0) |
| Saturday 20 January 2001 |
| Nationwide Division Three |
| Darlington |
0 (0) |
Chesterfield |
3 (2) |
| Saturday 6 January 2001 |
| Nationwide Division Three |
| Shrewsbury |
0 (0) |
Chesterfield |
0 (0) |
| Saturday 23 December 2000 |
| Nationwide Division Three |
| Torquay |
0 (0) |
Chesterfield |
0 (0) |
| Saturday 16 December 2000 |
| Nationwide Division Three |
| Southend |
3 (2) |
Chesterfield |
2 (1) |
| Tuesday 5 December 2000 |
| LDV Vans Trophy Northern Section - First Round |
| Rotherham |
3 (0) |
Chesterfield |
3 (3) |
| Saturday 25 November 2000 |
| Nationwide Division Three |
| Halifax |
2 (0) |
Chesterfield |
2 (0) |
| Saturday 4 November 2000 |
| Nationwide Division Three |
| Lincoln City |
1 (0) |
Chesterfield |
1 (0) |
| Tuesday 24 October 2000 |
| Nationwide Division Three |
| Kidderminster |
0 (0) |
Chesterfield |
2 (1) |
| Tuesday 17 October 2000 |
| Nationwide Division Three |
| Rochdale |
2 (1) |
Chesterfield |
2 (2) |
| Saturday 14 October 2000 |
| Nationwide Division Three |
| Exeter |
1 (0) |
Chesterfield |
1 (1) |
| Wednesday 27 September 2000 |
| Worthington Cup Second Round 2nd Leg |
| Fulham |
4 (1) |
Chesterfield |
0 (0) |
| Saturday 23 September 2000 |
| Nationwide Division Three |
| Blackpool |
1 (0) |
Chesterfield |
3 (2) |
| Tuesday 12 September 2000 |
| Nationwide Division Three |
| Carlisle |
2 (1) |
Chesterfield |
4 (3) |
| Saturday 9 September 2000 |
| Nationwide Division Three |
| Cheltenham |
0 (0) |
Chesterfield |
1 (0) |
| Monday 28 August 2000 |
| Nationwide Division Three |
| Scunthorpe |
1 (0) |
Chesterfield |
1 (0) |
| Tuesday 22 August 2000 |
| Worthington Cup First Round 1st Leg |
| Port Vale |
1 (1) |
Chesterfield |
2 (2) |
| Saturday 19 August 2000 |
| Nationwide Division Three |
| Hartlepool |
1 (1) |
Chesterfield |
2 (1) |
