| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 2nd Round | Sat 01 Dec | Tranmere Rvs. | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Tue 14 Aug | Chesterfield | 1 - 2 | Tranmere Rvs. |
| after extra time, 90 minutes 0-0 |
| (Associate Members) | Northern 2nd Round | Tue 09 Oct | Doncaster Rvs. | 1 - 0 | Chesterfield |
| 2011/2012 | F.A. Cup | 1st Round | Sat 12 Nov | Chesterfield | 1 - 3 | Torquay Utd. |
| League Cup | 1st Round | Tue 09 Aug | Rochdale | 3 - 2 | Chesterfield |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Final | Sun 25 Mar | Chesterfield | 2 - 0 | Swindon Town |
| played at Wembley |
| 2010/2011 | F.A. Cup | 2nd Round | Sat 27 Nov | Burton Albion | 3 - 1 | Chesterfield |
| League Cup | 1st Round | Tue 10 Aug | Chesterfield | 1 - 2 | Middlesbrough |
| (Associate Members) | Northern 2nd Round | Wed 06 Oct | Sheff. Wed. | 2 - 2 | Chesterfield |
| Sheffield Wednesday won 8-7 on penalties |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Chesterfield | 1 - 3 | Bournemouth |
| League Cup | 1st Round | Tue 11 Aug | Scunthorpe U. | 2 - 1 | Chesterfield |
| (Associate Members) | Northern Quarter-Final | Tue 10 Nov | Chesterfield | 1 - 3 | Carlisle Utd. |
| 2008/2009 | F.A. Cup | 3rd Round | Sat 03 Jan | Ipswich Town | 3 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 12 Aug | Preston N.E. | 2 - 0 | Chesterfield |
| (Associate Members) | Northern 1st Round | Wed 03 Sep | Chesterfield | 2 - 2 | Grimsby Town |
| no extra time, Grimsby Town won 4-1 on penalties |
| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | Chesterfield | 1 - 2 | Tranmere Rvs. |
| League Cup | 1st Round | Tue 14 Aug | Sheff. Utd. | 3 - 1 | Chesterfield |
| (Associate Members) | Northern 1st Round | Tue 04 Sep | Chesterfield | 1 - 3 | Hartlepool U. |
| 2006/2007 | F.A. Cup | 1st Round | Sat 11 Nov | Chesterfield | 0 - 1 | Basingstoke T. |
| League Cup | 4th Round | Tue 07 Nov | Chesterfield | 3 - 3 | Charlton Ath. |
| after extra time, 90 minutes 2-2, Charlton Athletic won 4-3 on penalties |
| (Associate Members) | Northern Semi-Final | Wed 10 Jan | Chesterfield | 2 - 4 | Crewe Alex. |
| 2005/2006 | F.A. Cup | 1st Round Replay | Wed 16 Nov | Chesterfield | 1 - 2 | Leyton Orient |
| League Cup | 1st Round | Wed 24 Aug | Chesterfield | 2 - 4 | Huddersfield |
| (Associate Members) | Northern 1st Round | Tue 18 Oct | Macclesfield | 2 - 0 | Chesterfield |
| 2004/2005 | F.A. Cup | 1st Round | Sat 13 Nov | Scunthorpe U. | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 24 Aug | Rotherham U. | 2 - 1 | Chesterfield |
| (Associate Members) | Northern 1st Round | Tue 28 Sep | Macclesfield | 2 - 1 | Chesterfield |
| 2003/2004 | F.A. Cup | 1st Round | Sat 08 Nov | Tranmere Rvs. | 3 - 2 | Chesterfield |
| League Cup | 1st Round | Tue 12 Aug | Chesterfield | 0 - 0 | Burnley |
| after extra time, 90 minutes 0-0, Burnley won 3-2 on penalties |
| (Associate Members) | Northern 2nd Round | Tue 04 Nov | Lincoln City | 4 - 3 | Chesterfield |
| after extra time, 90 minutes 3-3, Lincoln City won on silver goal rule |
| 2002/2003 | F.A. Cup | 1st Round | Sat 16 Nov | Chesterfield | 1 - 2 | Morecambe |
| League Cup | 2nd Round | Tue 01 Oct | Chesterfield | 1 - 1 | West Ham Utd. |
| (Associate Members) | Northern 2nd Round | Tue 12 Nov | Port Vale | 1 - 1 | Chesterfield |
| after extra time, 90 minutes 1-1, Port Vale won 4-3 on penalties |
| 2001/2002 | F.A. Cup | 2nd Round Replay | Tue 18 Dec | Southend Utd. | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 21 Aug | Port Vale | 2 - 1 | Chesterfield |
| (Associate Members) | Northern Quarter-Final | Tue 04 Dec | Chesterfield | 0 - 3 | Blackpool |
| 2000/2001 | F.A. Cup | 1st Round | Sat 18 Nov | Chesterfield | 0 - 1 | Bristol City |
| League Cup | 2nd Round | Wed 27 Sep | Fulham | 4 - 0 | Chesterfield |
| (Associate Members) | Northern Semi-Final | Tue 13 Feb | Lincoln City | 4 - 1 | Chesterfield |
| 1999/2000 | F.A. Cup | 1st Round | Sat 30 Oct | Chesterfield | 1 - 2 | Enfield |
| League Cup | 2nd Round | Tue 21 Sep | Middlesbrough | 2 - 1 | Chesterfield |
| Middlesbrough won 2-1 on aggregate |
| (Associate Members) | Northern Semi-Final | Tue 15 Feb | Chesterfield | 0 - 1 | Stoke City |
| 1998/1999 | F.A. Cup | 1st Round | Sat 14 Nov | Wycombe Wdrs. | 1 - 0 | Chesterfield |
| League Cup | 2nd Round | Tue 22 Sep | Chesterfield | 1 - 3 | Leicester City |
| Leicester City won 6-1 on aggregate |
| (Associate Members) | Northern Quarter-Final | Tue 19 Jan | Wrexham | 3 - 2 | Chesterfield |
| 1997/1998 | F.A. Cup | 2nd Round Replay | Tue 16 Dec | Chesterfield | 0 - 2 | Grimsby Town |
| League Cup | 2nd Round | Tue 30 Sep | Barnsley | 4 - 1 | Chesterfield |
| Barnsley won 6-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 09 Dec | Chesterfield | 0 - 1 | Grimsby Town |
| 1996/1997 | F.A. Cup | Semi Final Replay | Tue 22 Apr | Middlesbrough | 3 - 0 | Chesterfield |
| played at Hillsborough |
| League Cup | 1st Round | Tue 03 Sep | Chesterfield | 1 - 2 | Stockport Co. |
| Stockport County won 4-2 on aggregate |
| (Associate Members) | Northern 1st Round | Mon 09 Dec | Chesterfield | 0 - 2 | Preston N.E. |
| 1995/1996 | F.A. Cup | 2nd Round | Sat 02 Dec | Wrexham | 3 - 2 | Chesterfield |
| League Cup | 1st Round | Tue 05 Sep | Bury | 2 - 1 | Chesterfield |
| Bury won 3-1 on aggregate |
| (Associate Members) | Northern Semi-Final | Tue 30 Jan | Carlisle Utd. | 1 - 0 | Chesterfield |
| 1994/1995 | F.A. Cup | 1st Round Replay | Tue 22 Nov | Scarborough | 2 - 0 | Chesterfield |
| League Cup | 2nd Round | Tue 27 Sep | Wolves | 1 - 1 | Chesterfield |
| Wolverhampton Wanderers won 4-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 29 Nov | Carlisle Utd. | 1 - 0 | Chesterfield |
| 1993/1994 | F.A. Cup | 1st Round | Sat 13 Nov | Chesterfield | 0 - 1 | Rochdale |
| League Cup | 2nd Round | Tue 05 Oct | Chesterfield | 0 - 2 | West Ham Utd. |
| West Ham United won 7-1 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Six | Tue 09 Nov | Chesterfield | 1 - 2 | Lincoln City |
| 1992/1993 | F.A. Cup | 1st Round Replay | Wed 25 Nov | Chesterfield | 2 - 2 | Macclesfield |
| after extra time, 90 minutes ?-?, Macclesfield Town won 3-2 on penalties |
| League Cup | 2nd Round | Tue 06 Oct | Chesterfield | 1 - 4 | Liverpool |
| (Associate Members) | Northern Semi-Final | Tue 23 Feb | Stockport Co. | 2 - 1 | Chesterfield |
| 1991/1992 | F.A. Cup | 1st Round | Sat 16 Nov | Darlington | 2 - 1 | Chesterfield |
| League Cup | 1st Round | Tue 27 Aug | Chesterfield | 1 - 2 | Stoke City |
| Stoke City won 3-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 14 Jan | Bury | 2 - 1 | Chesterfield |
| 1990/1991 | F.A. Cup | 2nd Round | Tue 11 Dec | Chesterfield | 3 - 4 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 11 Sep | Hartlepool U. | 2 - 2 | Chesterfield |
| Hartlepool United won 4-3 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Five | Tue 18 Dec | Scunthorpe U. | 3 - 1 | Chesterfield |
| 1989/1990 | F.A. Cup | 2nd Round | Sat 09 Dec | Chesterfield | 0 - 2 | Huddersfield |
| League Cup | 1st Round | Tue 29 Aug | Chesterfield | 1 - 1 | Birmingham C. |
| Birmingham City won 3-2 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Eight | Tue 12 Dec | Chesterfield | 2 - 1 | Halifax Town |
| 1988/1989 | F.A. Cup | 1st Round Replay | Mon 28 Nov | Chesterfield | 2 - 3 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 06 Sep | Chesterfield | 1 - 1 | Port Vale |
| Port Vale won 4-3 on aggregate |
| (Associate Members) | Southern Quarter-Final | Tue 21 Feb | Chesterfield | 0 - 1 | Brentford |
| 1987/1988 | F.A. Cup | 1st Round Replay | Tue 17 Nov | Chesterfield | 0 - 1 | Notts. County |
| League Cup | 1st Round | Wed 26 Aug | Peterborough | 2 - 0 | Chesterfield |
| Peterborough United won 3-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 19 Jan | Halifax Town | 2 - 1 | Chesterfield |
| after extra time, 90 minutes 1-1 |
| 1986/1987 | F.A. Cup | 1st Round | Sat 15 Nov | Walsall | 2 - 0 | Chesterfield |
| League Cup | 1st Round | Tue 02 Sep | Wrexham | 2 - 2 | Chesterfield |
| Wrexham won 4-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 27 Jan | Rochdale | 3 - 0 | Chesterfield |
