Football League Cup 2019/20, Second round |
 | 10.09.2019 | | Grimsby Town | – | Macclesfield Town | | 0:0,
pen. 5:4 |
| Cleethorpes |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Blackpool | – | Macclesfield Town | | 2:2 (1:1),
pen. 2:4 |
| Blackpool |
Football League Cup 2018/19, Third round |
| 26.09.2018 | | West Ham United | – | Macclesfield Town | | 8:0 (3:0) |
| London |
Football League Cup 2018/19, Second round |
| 28.08.2018 | | Walsall | – | Macclesfield Town | | 3:3 (1:2),
pen. 1:3 |
| Walsall |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Macclesfield Town | – | Bradford City | | 1:1 (0:0),
pen. 4:2 |
| Macclesfield |
Football League Cup 2011/12, Second round |
| 24.08.2011 | | Bolton Wanderers | – | Macclesfield Town | | 2:1 (0:1) |
| Bolton |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Hull City | – | Macclesfield Town | | 0:2 (0:1) |
| Kingston upon Hull |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Leicester City | – | Macclesfield Town | | 4:3 (1:1) |
| Leicester |
Football League Cup 2009/10, First Round |
| 12.08.2009 | | Macclesfield Town | – | Leicester City | | 0:2 (0:0) |
| Macclesfield |
Football League Cup 2008/09, Second round |
| 27.08.2008 | | West Ham United | – | Macclesfield Town | | 4:1 aet
(0:1, 1:1) |
| London |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Macclesfield Town | – | Blackpool | | 2:0 (1:0) |
| Macclesfield |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Macclesfield Town | – | Leeds United | | 0:1 (0:0) |
| Macclesfield |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Leicester City | – | Macclesfield Town | | 2:0 (1:0) |
| Leicester |
Football League Cup 2005/06, Second round |
| 20.09.2005 | | Cardiff City | – | Macclesfield Town | | 2:1 (0:1) |
| Cardiff |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Nottingham Forest | – | Macclesfield Town | | 2:3 (1:2) |
| Nottingham |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Hartlepool | – | Macclesfield Town | | 2:1 (0:0) |
| Hartlepool |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Macclesfield Town | – | Sheffield United | | 1:2 (1:1) |
| Macclesfield |
Football League Cup 2002/03, Second round |
| 01.10.2002 | | Macclesfield Town | – | Preston North End | | 1:2 (1:1) |
| Macclesfield |
Football League Cup 2002/03, First Round |
| 11.09.2002 | | Macclesfield Town | – | Barnsley | | 4:1 aet
(1:0, 1:1) |
| Macclesfield |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Macclesfield Town | – | Bradford City | | 1:2 aet
(0:0, 1:1) |
| Macclesfield |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Macclesfield Town | – | Middlesbrough | | 1:3 (1:1) |
| Macclesfield |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Middlesbrough | – | Macclesfield Town | | 2:1 (0:0) |
| Middlesbrough |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Macclesfield Town | – | Bolton Wanderers | | 3:1 (2:0) |
| Macclesfield |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Bolton Wanderers | – | Macclesfield Town | | 1:0 (0:0) |
| Bolton |
Football League Cup 1999/00, First Round |
| 25.08.1999 | | Stoke City | – | Macclesfield Town | | 3:0 (0:0) |
| Stoke-on-Trent |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Macclesfield Town | – | Stoke City | | 1:1 (0:1) |
| Macclesfield |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Birmingham City | – | Macclesfield Town | | 6:0 (3:0) |
| Birmingham |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Macclesfield Town | – | Birmingham City | | 0:3 (0:0) |
| Macclesfield |
Football League Cup 1998/99, First Round |
| 19.08.1998 | | Stoke City | – | Macclesfield Town | | 1:0 (0:0) |
| Stoke-on-Trent |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Macclesfield Town | – | Stoke City | | 3:1 (1:1) |
| Macclesfield |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Hull City | – | Macclesfield Town | | 2:1 aet
(1:1, 1:1) |
| Kingston upon Hull |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Macclesfield Town | – | Hull City | | 0:0 |
| Macclesfield |
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