| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 4th Round | Sat 26 Jan | Bolton Wdrs. | 1 - 2 | Everton |
| League Cup | 2nd Round | Tue 28 Aug | Crawley Town | 2 - 1 | Bolton Wdrs. |
| 2011/2012 | F.A. Cup | 6th Round | Tue 27 Mar | Tottenham H. | 3 - 1 | Bolton Wdrs. |
| League Cup | 4th Round | Tue 25 Oct | Arsenal | 2 - 1 | Bolton Wdrs. |
| 2010/2011 | F.A. Cup | Semi Final | Sun 17 Apr | Bolton Wdrs. | 0 - 5 | Stoke City |
| played at Wembley |
| League Cup | 3rd Round | Tue 21 Sep | Burnley | 1 - 0 | Bolton Wdrs. |
| 2009/2010 | F.A. Cup | 5th Round Replay | Wed 24 Feb | Tottenham H. | 4 - 0 | Bolton Wdrs. |
| League Cup | 4th Round | Wed 28 Oct | Chelsea | 4 - 0 | Bolton Wdrs. |
| 2008/2009 | F.A. Cup | 3rd Round | Sat 03 Jan | Sunderland | 2 - 1 | Bolton Wdrs. |
| League Cup | 2nd Round | Tue 26 Aug | Bolton Wdrs. | 1 - 2 | Northampton |
| 2007/2008 | UEFA Cup | Last 16 Knockout Stage | Thu 13 Mar | Sport. Lisbon | 1 - 0 | Bolton Wdrs. |
| Sporting Lisbon won 2-1 on aggregate |
| F.A. Cup | 3rd Round | Sat 05 Jan | Bolton Wdrs. | 0 - 1 | Sheff. Utd. |
| League Cup | 4th Round | Wed 31 Oct | Bolton Wdrs. | 0 - 1 | Man. City |
| 2006/2007 | F.A. Cup | 4th Round Replay | Wed 14 Feb | Bolton Wdrs. | 1 - 3 | Arsenal |
| after extra time, 90 minutes 1-1 |
| League Cup | 3rd Round | Wed 25 Oct | Charlton Ath. | 1 - 0 | Bolton Wdrs. |
| 2005/2006 | UEFA Cup | Last 32 Knockout Stage | Thu 23 Feb | Marseille | 2 - 1 | Bolton Wdrs. |
| Marseille won 2-1 on aggregate |
| F.A. Cup | 5th Round Replay | Wed 15 Mar | West Ham Utd. | 2 - 1 | Bolton Wdrs. |
| League Cup | Quarter Final | Tue 20 Dec | Wigan Ath. | 2 - 0 | Bolton Wdrs. |
| 2004/2005 | F.A. Cup | 6th Round | Sat 12 Mar | Bolton Wdrs. | 0 - 1 | Arsenal |
| League Cup | 3rd Round | Wed 27 Oct | Bolton Wdrs. | 3 - 4 | Tottenham H. |
| after extra time, 90 minutes 2-2 |
| 2003/2004 | F.A. Cup | 3rd Round Replay | Tue 13 Jan | Bolton Wdrs. | 1 - 2 | Tranmere Rvs. |
| after extra time, 90 minutes 1-1 |
| League Cup | Final | Sun 29 Feb | Middlesbrough | 2 - 1 | Bolton Wdrs. |
| played at Millennium Stadium, Cardiff |
| 2002/2003 | F.A. Cup | 3rd Round Replay | Tue 14 Jan | Sunderland | 2 - 0 | Bolton Wdrs. |
| after extra time, 90 minutes 0-0 |
| League Cup | 2nd Round | Wed 02 Oct | Bolton Wdrs. | 0 - 1 | Bury |
| 2001/2002 | F.A. Cup | 4th Round | Tue 05 Feb | Tottenham H. | 4 - 0 | Bolton Wdrs. |
| League Cup | Quarter Final | Tue 11 Dec | Tottenham H. | 6 - 0 | Bolton Wdrs. |
| 2000/2001 | F.A. Cup | 5th Round Replay | Wed 07 Mar | Blackburn R. | 3 - 0 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 05 Sep | Macclesfield | 3 - 1 | Bolton Wdrs. |
| 1999/2000 | F.A. Cup | Semi Final | Sun 02 Apr | Aston Villa | 0 - 0 | Bolton Wdrs. |
| after extra time, 90 minutes 0-0, Aston Villa won 4-1 on penalties; played at Wembley |
| League Cup | Semi Final | Wed 26 Jan | Tranmere Rvs. | 3 - 0 | Bolton Wdrs. |
| Tranmere Rovers won 4-0 on aggregate |
| 1998/1999 | F.A. Cup | 3rd Round | Sat 02 Jan | Bolton Wdrs. | 1 - 2 | Wolves |
| League Cup | 4th Round | Tue 10 Nov | Bolton Wdrs. | 1 - 2 | Wimbledon |
| 1997/1998 | F.A. Cup | 3rd Round | Sat 03 Jan | Barnsley | 1 - 0 | Bolton Wdrs. |
| League Cup | 4th Round | Tue 18 Nov | Middlesbrough | 2 - 1 | Bolton Wdrs. |
| after extra time, 90 minutes 1-1 |
| 1996/1997 | F.A. Cup | 4th Round | Tue 04 Feb | Bolton Wdrs. | 2 - 3 | Chesterfield |
| League Cup | Quarter Final | Wed 08 Jan | Bolton Wdrs. | 0 - 2 | Wimbledon |
| 1995/1996 | F.A. Cup | 4th Round | Wed 14 Feb | Bolton Wdrs. | 0 - 1 | Leeds Utd. |
| League Cup | 4th Round Replay | Wed 20 Dec | Bolton Wdrs. | 0 - 0 | Norwich City |
| after extra time, 90 minutes 0-0, Norwich City won 3-2 on penalties |
| 1994/1995 | F.A. Cup | 3rd Round | Sat 07 Jan | Portsmouth | 3 - 1 | Bolton Wdrs. |
| League Cup | Final | Sun 02 Apr | Liverpool | 2 - 1 | Bolton Wdrs. |
| played at Wembley |
| 1993/1994 | F.A. Cup | 6th Round | Sat 12 Mar | Bolton Wdrs. | 0 - 1 | Oldham Ath. |
| League Cup | 2nd Round | Wed 06 Oct | Sheff. Wed. | 1 - 0 | Bolton Wdrs. |
| Sheffield Wednesday won 2-1 on aggregate |
| 1992/1993 | F.A. Cup | 5th Round | Sat 13 Feb | Derby County | 3 - 1 | Bolton Wdrs. |
| League Cup | 2nd Round | Tue 06 Oct | Wimbledon | 0 - 1 | Bolton Wdrs. |
| (Associate Members) | Northern Quarter-Final | Tue 02 Feb | Huddersfield | 3 - 0 | Bolton Wdrs. |
| 1991/1992 | F.A. Cup | 5th Round Replay | Wed 26 Feb | Southampton | 3 - 2 | Bolton Wdrs. |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 08 Oct | Bolton Wdrs. | 2 - 5 | Nottm. Forest |
| Nottingham Forest won 9-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 14 Jan | Crewe Alex. | 2 - 0 | Bolton Wdrs. |
| 1990/1991 | F.A. Cup | 4th Round | Sat 26 Jan | Man. Utd. | 1 - 0 | Bolton Wdrs. |
| League Cup | 2nd Round | Tue 09 Oct | Bolton Wdrs. | 2 - 3 | Coventry City |
| Coventry City won 7-4 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Two | Tue 18 Dec | Blackpool | 3 - 0 | Bolton Wdrs. |
| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | Blackpool | 2 - 1 | Bolton Wdrs. |
| League Cup | 3rd Round 2nd Replay | Tue 14 Nov | Bolton Wdrs. | 1 - 1 | Swindon Town |
| after extra time, 90 minutes ?-? |
| (Associate Members) | Northern Semi-Final | Tue 20 Feb | Tranmere Rvs. | 2 - 1 | Bolton Wdrs. |
| 1988/1989 | F.A. Cup | 2nd Round | Sat 10 Dec | Bolton Wdrs. | 1 - 2 | Port Vale |
| League Cup | 1st Round | Wed 07 Sep | Chester City | 3 - 1 | Bolton Wdrs. |
| Chester City won 3-2 on aggregate |
| (Associate Members) | Final | Sun 28 May | Bolton Wdrs. | 1 - 4 | Torquay Utd. |
| at Wembley |
| 1987/1988 | F.A. Cup | 3rd Round | Sat 09 Jan | Barnsley | 3 - 1 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 25 Aug | Bolton Wdrs. | 1 - 3 | Wigan Ath. |
| Wigan Athletic won 5-4 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 19 Jan | Bury | 1 - 0 | Bolton Wdrs. |
| 1986/1987 | F.A. Cup | 3rd Round | Sat 10 Jan | Coventry City | 3 - 0 | Bolton Wdrs. |
| League Cup | 1st Round | Tue 02 Sep | Bolton Wdrs. | 0 - 0 | Bury |
| Bury won 2-1 on aggregate |
| (Associate Members) | Northern Quarter-Final | Tue 10 Feb | Bolton Wdrs. | 1 - 2 | Chester City |
