| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 4th Round | Sat 26 Jan | Macclesfield | 0 - 1 | Wigan Ath. |
| Trophy | 1st Round | Fri 23 Nov | Gateshead | 2 - 0 | Macclesfield |
| 2011/2012 | F.A. Cup | 3rd Round Replay | Tue 17 Jan | Bolton Wdrs. | 2 - 0 | Macclesfield |
| League Cup | 2nd Round | Wed 24 Aug | Bolton Wdrs. | 2 - 1 | Macclesfield |
| (Associate Members) | Northern 2nd Round | Wed 05 Oct | Crewe Alex. | 1 - 0 | Macclesfield |
| 2010/2011 | F.A. Cup | 2nd Round | Sat 27 Nov | Huddersfield | 6 - 0 | Macclesfield |
| League Cup | 1st Round | Tue 10 Aug | Leicester City | 4 - 3 | Macclesfield |
| (Associate Members) | Northern 2nd Round | Tue 05 Oct | Macclesfield | 2 - 4 | Crewe Alex. |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Milton Keynes | 1 - 0 | Macclesfield |
| League Cup | 1st Round | Wed 12 Aug | Macclesfield | 0 - 2 | Leicester City |
| (Associate Members) | Northern 2nd Round | Tue 06 Oct | Carlisle Utd. | 4 - 2 | Macclesfield |
| 2008/2009 | F.A. Cup | 3rd Round | Sat 03 Jan | Macclesfield | 0 - 1 | Everton |
| League Cup | 2nd Round | Wed 27 Aug | West Ham Utd. | 4 - 1 | Macclesfield |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern 1st Round | Tue 02 Sep | Crewe Alex. | 3 - 0 | Macclesfield |
| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | Rushden & D. | 3 - 1 | Macclesfield |
| League Cup | 1st Round | Tue 14 Aug | Macclesfield | 0 - 1 | Leeds Utd. |
| (Associate Members) | Northern 2nd Round | Tue 09 Oct | Macclesfield | 0 - 1 | Stockport Co. |
| 2006/2007 | F.A. Cup | 3rd Round | Sat 06 Jan | Chelsea | 6 - 1 | Macclesfield |
| League Cup | 1st Round | Tue 22 Aug | Leicester City | 2 - 0 | Macclesfield |
| (Associate Members) | Northern 1st Round | Tue 17 Oct | Macclesfield | 0 - 1 | Stockport Co. |
| 2005/2006 | F.A. Cup | 1st Round Replay | Tue 15 Nov | Yeovil Town | 4 - 0 | Macclesfield |
| League Cup | 2nd Round | Tue 20 Sep | Cardiff City | 2 - 1 | Macclesfield |
| (Associate Members) | Northern Final | Tue 07 Mar | Macclesfield | 3 - 2 | Carlisle Utd. |
| after extra time, 90 minutes 2-1, Carlisle United won on away goals rule |
| 2004/2005 | F.A. Cup | 2nd Round | Sat 04 Dec | Hull City | 4 - 0 | Macclesfield |
| League Cup | 1st Round | Tue 24 Aug | Hartlepool U. | 2 - 1 | Macclesfield |
| (Associate Members) | Northern Quarter-Final | Tue 30 Nov | Macclesfield | 0 - 1 | Tranmere Rvs. |
| 2003/2004 | F.A. Cup | 3rd Round | Sat 03 Jan | Swansea City | 2 - 1 | Macclesfield |
| League Cup | 1st Round | Tue 12 Aug | Macclesfield | 1 - 2 | Sheff. Utd. |
| (Associate Members) | Northern 1st Round | Tue 14 Oct | Chesterfield | 2 - 1 | Macclesfield |
| 2002/2003 | F.A. Cup | 3rd Round | Sat 04 Jan | Macclesfield | 0 - 2 | Watford |
| League Cup | 2nd Round | Tue 01 Oct | Macclesfield | 1 - 2 | Preston N.E. |
| (Associate Members) | Northern 2nd Round | Tue 12 Nov | Macclesfield | 1 - 2 | Tranmere Rvs. |
| after extra time, 90 minutes 1-1, Tranmere Rovers won on golden goal rule |
| 2001/2002 | F.A. Cup | 3rd Round | Sun 06 Jan | Macclesfield | 0 - 3 | West Ham Utd. |
| League Cup | 1st Round | Tue 21 Aug | Macclesfield | 1 - 2 | Bradford City |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern 1st Round | Tue 16 Oct | Darlington | 2 - 1 | Macclesfield |
| 2000/2001 | F.A. Cup | 1st Round | Sat 18 Nov | Macclesfield | 0 - 1 | Oxford Utd. |
| League Cup | 2nd Round | Tue 26 Sep | Macclesfield | 1 - 3 | Middlesbrough |
| Middlesbrough won 5-2 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 09 Jan | Chesterfield | 4 - 1 | Macclesfield |
| 1999/2000 | F.A. Cup | 1st Round Replay | Tue 09 Nov | Hull City | 4 - 0 | Macclesfield |
| League Cup | 1st Round | Wed 25 Aug | Stoke City | 3 - 0 | Macclesfield |
| Stoke City won 4-1 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 11 Jan | Rochdale | 3 - 2 | Macclesfield |
| after extra time, 90 minutes 2-2, Rochdale won on golden goal rule |
| 1998/1999 | F.A. Cup | 3rd Round | Sat 02 Jan | Coventry City | 7 - 0 | Macclesfield |
| League Cup | 2nd Round | Tue 22 Sep | Birmingham C. | 6 - 0 | Macclesfield |
| Birmingham City won 9-0 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 08 Dec | Macclesfield | 0 - 1 | Wrexham |
| 1997/1998 | F.A. Cup | 2nd Round | Sat 06 Dec | Macclesfield | 0 - 7 | Walsall |
| League Cup | 1st Round | Tue 26 Aug | Hull City | 2 - 1 | Macclesfield |
| after extra time, 90 minutes 1-1, Hull City won 2-1 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 13 Jan | Macclesfield | 0 - 1 | Preston N.E. |
| 1996/1997 | F.A. Cup | 1st Round | Sat 16 Nov | Macclesfield | 0 - 2 | Rochdale |
| 1993/1994 | F.A. Cup | 2nd Round | Sat 04 Dec | Crewe Alex. | 2 - 1 | Macclesfield |
| 1992/1993 | F.A. Cup | 2nd Round | Sat 05 Dec | Macclesfield | 0 - 2 | Stockport Co. |
| 1989/1990 | F.A. Cup | 1st Round Replay | Tue 21 Nov | Chester City | 3 - 2 | Macclesfield |
| 1987/1988 | F.A. Cup | 3rd Round | Sun 10 Jan | Port Vale | 1 - 0 | Macclesfield |
