| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 1st Round | Sat 03 Nov | Swindon Town | 0 - 2 | Macclesfield |
| League Cup | 4th Round | Tue 30 Oct | Swindon Town | 2 - 3 | Aston Villa |
| (Associate Members) | Southern 1st Round | Wed 05 Sep | Oxford Utd. | 1 - 0 | Swindon Town |
| 2011/2012 | F.A. Cup | 4th Round | Sat 28 Jan | Leicester City | 2 - 0 | Swindon Town |
| League Cup | 2nd Round | Tue 30 Aug | Swindon Town | 1 - 3 | Southampton |
| (Associate Members) | Final | Sun 25 Mar | Chesterfield | 2 - 0 | Swindon Town |
| played at Wembley |
| 2010/2011 | F.A. Cup | 2nd Round Replay | Tue 07 Dec | Swindon Town | 2 - 3 | Crawley Town |
| after extra time, 90 minutes 2-2 |
| League Cup | 1st Round | Tue 10 Aug | Swindon Town | 1 - 2 | Leyton Orient |
| (Associate Members) | Southern Quarter-Final | Tue 09 Nov | Swindon Town | 1 - 1 | Brentford |
| Brentford won 4-2 on penalties |
| 2009/2010 | F.A. Cup | 3rd Round | Sat 02 Jan | Fulham | 1 - 0 | Swindon Town |
| League Cup | 2nd Round | Tue 25 Aug | Wolves | 0 - 0 | Swindon Town |
| after extra time, Wolverhampton Wanderers won 6-5 on penalties |
| (Associate Members) | Southern Quarter-Final | Tue 10 Nov | Swindon Town | 0 - 0 | Norwich City |
| after extra time, Norwich City won 5-3 on penalties |
| 2008/2009 | F.A. Cup | 1st Round | Sat 08 Nov | Histon | 1 - 0 | Swindon Town |
| League Cup | 1st Round | Tue 12 Aug | Swindon Town | 2 - 3 | Q.P.R. |
| (Associate Members) | Southern Quarter-Final | Wed 12 Nov | Brighton & HA | 2 - 0 | Swindon Town |
| 2007/2008 | F.A. Cup | 3rd Round Replay | Tue 22 Jan | Barnet | 1 - 1 | Swindon Town |
| after extra time, 90 minutes 1-1, Barnet won 2-0 on penalties |
| League Cup | 1st Round | Tue 14 Aug | Swindon Town | 0 - 2 | Charlton Ath. |
| (Associate Members) | Southern 2nd Round | Tue 09 Oct | Swindon Town | 1 - 3 | Cheltenham T. |
| 2006/2007 | F.A. Cup | 3rd Round | Sat 06 Jan | Crystal Palace | 2 - 1 | Swindon Town |
| League Cup | 1st Round | Tue 22 Aug | Swindon Town | 2 - 2 | Brentford |
| after extra time, 90 minutes 2-2, Brentford win 4-3 on pens |
| (Associate Members) | Southern 1st Round | Tue 17 Oct | Wycombe Wdrs. | 1 - 0 | Swindon Town |
| 2005/2006 | F.A. Cup | 1st Round Replay | Wed 16 Nov | Boston Utd. | 4 - 1 | Swindon Town |
| League Cup | 1st Round | Tue 23 Aug | Swindon Town | 1 - 3 | Wycombe Wdrs. |
| (Associate Members) | Southern 2nd Round | Tue 22 Nov | Peterborough | 2 - 1 | Swindon Town |
| 2004/2005 | F.A. Cup | 2nd Round Replay | Wed 15 Dec | Notts. County | 2 - 0 | Swindon Town |
| League Cup | 2nd Round | Tue 21 Sep | Leeds Utd. | 1 - 0 | Swindon Town |
| (Associate Members) | Southern Semi-Final | Tue 25 Jan | Southend Utd. | 2 - 0 | Swindon Town |
| 2003/2004 | F.A. Cup | 1st Round | Sat 08 Nov | Wycombe Wdrs. | 4 - 1 | Swindon Town |
| League Cup | 2nd Round | Wed 24 Sep | Leeds Utd. | 2 - 2 | Swindon Town |
| after extra time, 90 minutes 2-2, Leeds United won 4-3 on penalties |
| (Associate Members) | Southern 1st Round | Wed 15 Oct | Boston Utd. | 2 - 1 | Swindon Town |
| 2002/2003 | F.A. Cup | 2nd Round | Sun 08 Dec | Oxford Utd. | 1 - 0 | Swindon Town |
| League Cup | 1st Round | Wed 11 Sep | Swindon Town | 1 - 2 | Wycombe Wdrs. |
| (Associate Members) | Southern 2nd Round | Tue 12 Nov | Kidderminster | 3 - 2 | Swindon Town |
| after extra time, 90 minutes 2-2, Kidderminster Harriers won on golden goal rule |
| 2001/2002 | F.A. Cup | 3rd Round | Sat 05 Jan | Man. City | 2 - 0 | Swindon Town |
| League Cup | 2nd Round | Tue 11 Sep | West Brom. | 2 - 0 | Swindon Town |
| after extra time, 90 minutes 0-0 |
| (Associate Members) | Southern 1st Round | Tue 16 Oct | Colchester U. | 1 - 0 | Swindon Town |
| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Swindon Town | 0 - 2 | Coventry City |
| League Cup | 2nd Round | Tue 26 Sep | Swindon Town | 0 - 1 | Tranmere Rvs. |
| Tranmere Rovers won 2-1 on aggregate |
| (Associate Members) | Southern Semi-Final | Tue 13 Feb | Southend Utd. | 2 - 1 | Swindon Town |
| after extra time, 90 minutes 1-1, Southend United won on the golden goal rule |
| 1999/2000 | F.A. Cup | 3rd Round | Sat 11 Dec | Charlton Ath. | 2 - 1 | Swindon Town |
| League Cup | 1st Round | Tue 24 Aug | Leyton Orient | 1 - 1 | Swindon Town |
| Leyton Orient won 2-1 on aggregate |
| 1998/1999 | F.A. Cup | 3rd Round Replay | Tue 19 Jan | Barnsley | 3 - 1 | Swindon Town |
| League Cup | 1st Round | Tue 18 Aug | Wycombe Wdrs. | 2 - 0 | Swindon Town |
| Wycombe Wanderers won 3-2 on aggregate |
| 1997/1998 | F.A. Cup | 3rd Round | Sat 03 Jan | Swindon Town | 1 - 2 | Stevenage B. |
| League Cup | 1st Round | Tue 26 Aug | Watford | 1 - 1 | Swindon Town |
| Watford won 3-1 on aggregate |
| 1996/1997 | F.A. Cup | 3rd Round | Sun 05 Jan | Everton | 3 - 0 | Swindon Town |
| League Cup | 3rd Round | Wed 23 Oct | Man. Utd. | 2 - 1 | Swindon Town |
| 1995/1996 | F.A. Cup | 5th Round Replay | Wed 28 Feb | Southampton | 2 - 0 | Swindon Town |
| League Cup | 2nd Round | Wed 04 Oct | Blackburn R. | 2 - 0 | Swindon Town |
| Blackburn Rovers won 5-2 on aggregate |
| (Associate Members) | Southern 1st Round | Wed 29 Nov | Swindon Town | 0 - 1 | Hereford Utd. |
| 1994/1995 | F.A. Cup | 4th Round | Sat 28 Jan | Watford | 1 - 0 | Swindon Town |
| League Cup | Semi Final | Wed 08 Mar | Bolton Wdrs. | 3 - 1 | Swindon Town |
| Bolton Wanderers won 4-3 on aggregate |
| Anglo-Italian Cup | Group A | Tue 15 Nov | Ascoli | 3 - 1 | Swindon Town |
| 1993/1994 | F.A. Cup | 3rd Round Replay | Tue 18 Jan | Ipswich Town | 2 - 1 | Swindon Town |
| after extra time, 90 minutes ?-? |
| League Cup | 3rd Round | Tue 26 Oct | Portsmouth | 2 - 0 | Swindon Town |
| 1992/1993 | F.A. Cup | 3rd Round | Mon 04 Jan | Q.P.R. | 3 - 0 | Swindon Town |
| League Cup | 3rd Round | Tue 27 Oct | Swindon Town | 0 - 1 | Oldham Ath. |
| 1991/1992 | F.A. Cup | 5th Round | Sun 16 Feb | Swindon Town | 1 - 2 | Aston Villa |
| League Cup | 4th Round | Tue 17 Dec | Swindon Town | 0 - 1 | Crystal Palace |
| 1990/1991 | F.A. Cup | 4th Round | Sat 26 Jan | Norwich City | 3 - 1 | Swindon Town |
| League Cup | 3rd Round Replay | Tue 06 Nov | Swindon Town | 0 - 1 | Sheff. Wed. |
| 1989/1990 | F.A. Cup | 3rd Round | Sat 06 Jan | Bristol City | 2 - 1 | Swindon Town |
| League Cup | 4th Round Replay | Tue 16 Jan | Southampton | 4 - 2 | Swindon Town |
| 1988/1989 | F.A. Cup | 4th Round Replay | Wed 01 Feb | West Ham Utd. | 1 - 0 | Swindon Town |
| League Cup | 2nd Round | Wed 12 Oct | Crystal Palace | 2 - 0 | Swindon Town |
| Crystal Palace won 4-1 on aggregate |
| 1987/1988 | F.A. Cup | 4th Round | Sat 30 Jan | Newcastle Utd. | 5 - 0 | Swindon Town |
| League Cup | 3rd Round Replay | Tue 03 Nov | Watford | 4 - 2 | Swindon Town |
| 1986/1987 | F.A. Cup | 4th Round | Tue 03 Feb | Swindon Town | 1 - 2 | Leeds Utd. |
| League Cup | 2nd Round | Wed 08 Oct | Swindon Town | 0 - 0 | Southampton |
| Southampton won 3-0 on aggregate |
| (Associate Members) | Southern Semi-Final | Tue 10 Mar | Swindon Town | 2 - 3 | Aldershot |
