FA Cup 2016/17, Second Round Proper |
 | 02.12.2016 |  | Macclesfield Town | – | Oxford United | | 0:0 |
| Macclesfield |
FA Cup 2014/15, Fourth Qualifying Round |
| 24.10.2014 | | Macclesfield Town | – | Wrexham |  | 1:1 (1:0) |
| Macclesfield |
FA Cup 2013/14, Third Round Proper |
| 04.01.2014 | | Macclesfield Town | – | Sheffield Wednesday | | 1:1 (0:1) |
| Macclesfield |
FA Cup 2012/13, Second Round Proper |
| 18.12.2012 | | Barrow | – | Macclesfield Town | | 1:1 (1:1) |
| Barrow-in-Furness |
FA Cup 2011/12, Third Round Proper |
| 07.01.2012 | | Macclesfield Town | – | Bolton Wanderers | | 2:2 (1:1) |
| Macclesfield |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Chelmsford City | – | Macclesfield Town | | 1:1 (1:0) |
| Chelmsford |
FA Cup 2010/11, First Round Proper |
| 16.11.2010 | | Southend United | – | Macclesfield Town | | 2:2 aet
(0:0, 1:1),
pen. 3:5 * |
| Southend-on-Sea |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Macclesfield Town | – | Southend United | | 2:2 (1:1) |
| Macclesfield |
FA Cup 2006/07, First Round Proper |
| 13.11.2006 | | Macclesfield Town | – | Walsall | | 0:0 |
| Macclesfield |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Macclesfield Town | – | Yeovil Town | | 1:1 (0:0) |
| Macclesfield |
FA Cup 2004/05, First Round Proper |
| 13.11.2004 | | Alfreton Town | – | Macclesfield Town | | 1:1 (0:0) |
| Alfreton |
FA Cup 2003/04, Second Round Proper |
| 16.12.2003 | | Cambridge United | – | Macclesfield Town | | 2:2 aet
(0:1, 1:1),
pen. 2:4 * |
| Cambridge |
FA Cup 2003/04, Second Round Proper |
| 06.12.2003 | | Macclesfield Town | – | Cambridge United | | 1:1 (1:1) |
| Macclesfield |
FA Cup 2001/02, First Round Proper |
| 28.11.2001 | | Forest Green Rovers | – | Macclesfield Town | | 1:1 aet
(1:1, 1:1),
pen. 10:11 * |
| Nailsworth |
FA Cup 2001/02, First Round Proper |
| 17.11.2001 | | Macclesfield Town | – | Forest Green Rovers | | 2:2 (1:1) |
| Macclesfield |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Macclesfield Town | – | Hull City | | 0:0 |
| Macclesfield |
FA Cup 1998/99, First Round Proper |
| 24.11.1998 | | Slough Town | – | Macclesfield Town | | 1:1 aet
(1:1, 1:1),
pen. 8:9 * |
| Slough |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Macclesfield Town | – | Slough Town | | 2:2 (0:2) |
| Macclesfield |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Bishop Auckland | – | Macclesfield Town | | 2:2 |
| |
FA Cup 1992/93, First Round Proper |
| 25.11.1992 | | Chesterfield | – | Macclesfield Town | | 2:2 aet,
pen. 2:3 * |
| Chesterfield |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | Macclesfield Town | – | Chesterfield | | 0:0 |
| Macclesfield |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Netherfield | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Hucknall Town | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Macclesfield Town | – | Altrincham | | 2:2 |
| |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Macclesfield Town | – | Chester City | | 1:1 |
| Macclesfield |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Macclesfield Town | – | Altrincham | | 0:0 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Macclesfield Town | – | Marine | | 0:0 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Stalybridge Celtic | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Macclesfield Town | – | York City | | 0:0 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Horwich Railway Mechanics Institute | – | Macclesfield Town | | 0:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Macclesfield Town | – | Mossley | | 0:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Rhyl | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Macclesfield Town | – | Sutton Town | | 0:0 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Macclesfield Town | – | Merthyr Tydfil | | 0:0 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Leek Town | – | Macclesfield Town | | 2:2 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Macclesfield Town | – | Scunthorpe United | | 1:1 (1:1) |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Stockport County | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Wigan Athletic | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Macclesfield Town | – | Nuneaton Borough | | 1:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Matlock Town | – | Macclesfield Town | | 2:2 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Northwich Victoria | – | Macclesfield Town | | 1:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Macclesfield Town | – | Droylsden | | 2:2 aet * |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Droylsden | – | Macclesfield Town | | 3:3 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Macclesfield Town | – | Linotype & Machinery | | 1:1 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Hyde United | – | Macclesfield Town | | 3:3 aet * |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Macclesfield Town | – | Hyde United | | 4:4 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Winsford United | – | Macclesfield Town | | 2:2 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Macclesfield Town | – | Buxton | | 0:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Droylsden United | – | Macclesfield Town | | 5:5 |
| |
