| Saturday 5 May 2001 |
| The Football Conference |
| Chester |
1 (0) |
Rushden & D'monds |
2 (0) |
| Thursday 3 May 2001 |
| Nationwide Variety Club Trophy Semi Final |
| Chester |
1 (1) |
Nuneaton |
1 (1) |
| Tuesday 1 May 2001 |
| The Football Conference |
| Chester |
3 (1) |
Scarborough |
2 (1) |
| Saturday 28 April 2001 |
| The Football Conference |
| Woking |
1 (0) |
Chester |
0 (0) |
| Thursday 26 April 2001 |
| The Football Conference |
| Chester |
0 (0) |
Kingstonian |
0 (0) |
| Tuesday 24 April 2001 |
| The Football Conference |
| Kettering |
4 (2) |
Chester |
0 (0) |
| Saturday 21 April 2001 |
| The Football Conference |
| Chester |
1 (0) |
Dag & Red |
1 (0) |
| Wednesday 18 April 2001 |
| The Football Conference |
| Leigh RMI |
0 (0) |
Chester |
1 (1) |
| Monday 16 April 2001 |
| The Football Conference |
| Stevenage |
1 (1) |
Chester |
2 (2) |
| Saturday 14 April 2001 |
| The Football Conference |
| Chester |
0 (0) |
Forest Green |
1 (0) |
| Tuesday 3 April 2001 |
| The Football Conference |
| Dover |
1 (1) |
Chester |
1 (0) |
| Tuesday 27 March 2001 |
| The Football Conference |
| Telford |
3 (2) |
Chester |
0 (0) |
| Friday 23 March 2001 |
| The Football Conference |
| Nuneaton |
1 (1) |
Chester |
2 (2) |
| Saturday 17 March 2001 |
| The Football Conference |
| Chester |
0 (0) |
Hednesford |
1 (0) |
| Tuesday 13 March 2001 |
| The Football Conference |
| Southport |
1 (1) |
Chester |
0 (0) |
| Saturday 3 March 2001 |
| The Football Conference |
| Hayes |
1 (0) |
Chester |
3 (1) |
| Tuesday 27 February 2001 |
| The Football Conference |
| Chester |
2 (0) |
Boston Utd |
2 (0) |
| Tuesday 20 February 2001 |
| The Football Conference |
| Chester |
1 (1) |
Telford |
0 (0) |
| Saturday 17 February 2001 |
| The Football Conference |
| Northwich |
1 (0) |
Chester |
1 (1) |
| Saturday 10 February 2001 |
| The Football Conference |
| Chester |
2 (2) |
Yeovil |
1 (0) |
| Tuesday 30 January 2001 |
| LDV Vans Trophy Northern Section - Second Round |
| Port Vale |
2 (1) |
Chester |
0 (0) |
| Saturday 27 January 2001 |
| The Football Conference |
| Chester |
1 (1) |
Morecambe |
0 (0) |
| Saturday 6 January 2001 |
| AXA-Sponsored FA Challenge Cup Third Round |
| Blackburn |
2 (0) |
Chester |
0 (0) |
| Monday 1 January 2001 |
| The Football Conference |
| Hereford |
2 (0) |
Chester |
0 (0) |
| Tuesday 26 December 2000 |
| The Football Conference |
| Chester |
2 (1) |
Hereford |
1 (0) |
| Saturday 23 December 2000 |
| The Football Conference |
| Chester |
0 (0) |
Hayes |
0 (0) |
| Saturday 16 December 2000 |
| The Football Conference |
| Doncaster |
1 (1) |
Chester |
0 (0) |
| Saturday 9 December 2000 |
| AXA-Sponsored FA Challenge Cup Second Round |
| Chester |
3 (1) |
Oxford Utd |
2 (2) |
| Tuesday 5 December 2000 |
| LDV Vans Trophy Northern Section - First Round |
| Chester |
1 (0) |
Hull |
0 (0) |
| Saturday 2 December 2000 |
| The Football Conference |
| Chester |
3 (2) |
Woking |
3 (3) |
| Tuesday 28 November 2000 |
| AXA-Sponsored FA Challenge Cup First Round |
| Plymouth |
1 (0) |
Chester |
1 (1) |
| Saturday 18 November 2000 |
| AXA-Sponsored FA Challenge Cup First Round |
| Chester |
1 (0) |
Plymouth |
1 (0) |
| Saturday 11 November 2000 |
| The Football Conference |
| Chester |
1 (0) |
Stevenage |
1 (0) |
| Saturday 4 November 2000 |
| The Football Conference |
| Dag & Red |
1 (0) |
Chester |
1 (0) |
| Saturday 21 October 2000 |
| The Football Conference |
| Chester |
1 (0) |
Leigh RMI |
1 (0) |
| Saturday 14 October 2000 |
| The Football Conference |
| Forest Green |
1 (0) |
Chester |
1 (0) |
| Sunday 8 October 2000 |
| The Football Conference |
| Chester |
2 (0) |
Kettering |
1 (0) |
| Tuesday 3 October 2000 |
| The Football Conference |
| Scarborough |
0 (0) |
Chester |
2 (1) |
| Saturday 30 September 2000 |
| The Football Conference |
| Hednesford |
0 (0) |
Chester |
0 (0) |
| Tuesday 26 September 2000 |
| The Football Conference |
| Chester |
4 (1) |
Nuneaton |
0 (0) |
| Saturday 23 September 2000 |
| The Football Conference |
| Kingstonian |
1 (0) |
Chester |
3 (1) |
| Tuesday 12 September 2000 |
| The Football Conference |
| Chester |
1 (0) |
Northwich |
1 (1) |
| Saturday 9 September 2000 |
| The Football Conference |
| Yeovil |
2 (1) |
Chester |
1 (0) |
| Tuesday 5 September 2000 |
| The Football Conference |
| Morecambe |
0 (0) |
Chester |
2 (1) |
| Saturday 2 September 2000 |
| The Football Conference |
| Chester |
0 (0) |
Southport |
1 (1) |
| Wednesday 30 August 2000 |
| The Football Conference |
| Boston Utd |
0 (0) |
Chester |
0 (0) |
| Saturday 26 August 2000 |
| The Football Conference |
| Chester |
1 (0) |
Dover |
0 (0) |
| Tuesday 22 August 2000 |
| The Football Conference |
| Chester |
3 (1) |
Doncaster |
0 (0) |
| Saturday 19 August 2000 |
| The Football Conference |
| Rushden & D'monds |
2 (0) |
Chester |
0 (0) |
