FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Alfreton Town | – | Macclesfield Town | | 3:1 (1:1) |
| Alfreton |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Coalville Town | – | Macclesfield Town | | 1:0 (0:0) |
| Coalville |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Squires Gate | – | Macclesfield Town | | 6:4 (2:2) |
| Squires Gate |
FA Cup 2019/20, First Round Proper |
| 10.11.2019 | | Macclesfield Town | – | Kingstonian | | 0:4 (0:2) |
| Macclesfield |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Maidstone United | – | Macclesfield Town | | 2:1 (0:1) |
| Maidstone |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Forest Green Rovers | – | Macclesfield Town | | 1:0 (1:0) |
| Nailsworth |
FA Cup 2016/17, Second Round Proper |
| 13.12.2016 | | Oxford United | – | Macclesfield Town | | 3:0 (1:0) * |
| Oxford |
FA Cup 2015/16, First Round Proper |
| 07.11.2015 | | Portsmouth | – | Macclesfield Town | | 2:1 (2:1) |
| Portsmouth |
FA Cup 2014/15, Fourth Qualifying Round |
| 28.10.2014 |  | Wrexham | – | Macclesfield Town | | 5:2 (2:1) * |
| Wrexham |
FA Cup 2013/14, Third Round Proper |
| 14.01.2014 | | Sheffield Wednesday | – | Macclesfield Town | | 4:1 (1:0) * |
| Sheffield |
FA Cup 2012/13, Fourth Round Proper |
| 26.01.2013 | | Macclesfield Town | – | Wigan Athletic | | 0:1 (0:1) |
| Macclesfield |
FA Cup 2011/12, Third Round Proper |
| 17.01.2012 | | Bolton Wanderers | – | Macclesfield Town | | 2:0 (2:0) * |
| Bolton |
FA Cup 2010/11, Second Round Proper |
| 27.11.2010 | | Huddersfield Town | – | Macclesfield Town | | 6:0 (3:0) |
| Huddersfield |
FA Cup 2009/10, First Round Proper |
| 07.11.2009 | | Milton Keynes Dons | – | Macclesfield Town | | 1:0 (1:0) |
| Milton Keynes |
FA Cup 2008/09, Third Round Proper |
| 03.01.2009 | | Macclesfield Town | – | Everton | | 0:1 (0:1) |
| Macclesfield |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Rushden & Diamonds | – | Macclesfield Town | | 3:1 (2:0) |
| Irthlingborough |
FA Cup 2006/07, Third Round Proper |
| 06.01.2007 | | Chelsea | – | Macclesfield Town | | 6:1 (2:1) |
| London |
FA Cup 2005/06, First Round Proper |
| 15.11.2005 | | Yeovil Town | – | Macclesfield Town | | 4:0 (1:0) * |
| Yeovil |
FA Cup 2004/05, Second Round Proper |
| 04.12.2004 | | Hull City | – | Macclesfield Town | | 4:0 (3:0) |
| Kingston upon Hull |
FA Cup 2003/04, Third Round Proper |
| 03.01.2004 | | Swansea City | – | Macclesfield Town | | 2:1 (1:0) |
| Swansea |
FA Cup 2002/03, Third Round Proper |
| 04.01.2003 | | Macclesfield Town | – | Watford | | 0:2 (0:1) |
| Macclesfield |
FA Cup 2001/02, Third Round Proper |
| 06.01.2002 | | Macclesfield Town | – | West Ham United | | 0:3 (0:1) |
| Macclesfield |
FA Cup 2000/01, First Round Proper |
| 18.11.2000 | | Macclesfield Town | – | Oxford United | | 0:1 (0:0) |
| Macclesfield |
FA Cup 1999/00, First Round Proper |
| 09.11.1999 | | Hull City | – | Macclesfield Town | | 4:0 (3:0) * |
| Kingston upon Hull |
FA Cup 1998/99, Third Round Proper |
| 02.01.1999 | | Coventry City | – | Macclesfield Town | | 7:0 (3:0) |
| Coventry |
FA Cup 1997/98, Second Round Proper |
| 06.12.1997 | | Macclesfield Town | – | Walsall | | 0:7 (0:2) |
| Macclesfield |
FA Cup 1996/97, First Round Proper |
| 16.11.1996 | | Macclesfield Town | – | Rochdale | | 0:2 (0:2) |
| Macclesfield |
FA Cup 1995/96, Fourth Qualifying Round |
| | | Macclesfield Town | – | Northwich Victoria | | 0:1 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Macclesfield Town | – | Bishop Auckland | | 0:1 * |
| |
FA Cup 1993/94, Second Round Proper |
| 04.12.1993 | | Crewe Alexandra | – | Macclesfield Town | | 2:1 (2:0) |
| Crewe |
FA Cup 1992/93, Second Round Proper |
| 05.12.1992 | | Macclesfield Town | – | Stockport County | | 0:2 (0:1) |
| Macclesfield |
FA Cup 1991/92, Second Qualifying Round |
| | | Macclesfield Town | – | Borrowash Victoria | | 1:2 |
| |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Altrincham | – | Macclesfield Town | | 3:0 * |
| |
FA Cup 1989/90, First Round Proper |
| 21.11.1989 | | Chester City | – | Macclesfield Town | | 3:2 * |
| Chester |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Altrincham | – | Macclesfield Town | | 4:0 * |
| |
FA Cup 1987/88, Third Round Proper |
| 10.01.1988 | | Port Vale | – | Macclesfield Town | | 1:0 (0:0) |
| Stoke-on-Trent |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Macclesfield Town | – | Southport | | 0:1 |
| |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Macclesfield Town | – | Hartlepool United | | 1:2 |
| |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Macclesfield Town | – | Port Vale | | 1:2 |
| |
FA Cup 1983/84, First Round Proper |
| 22.11.1983 | | York City | – | Macclesfield Town | | 2:0 * |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Macclesfield Town | – | Worcester City | | 1:5 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Witton Albion | – | Macclesfield Town | | 3:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Stourbridge | – | Macclesfield Town | | 6:2 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Mossley | – | Macclesfield Town | | 3:2 * |
| |
FA Cup 1978/79, Preliminary Round |
| | | Macclesfield Town | – | Marine | | 2:4 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Macclesfield Town | – | Mossley | | 0:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Macclesfield Town | – | Rhyl | | 1:2 * |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Sheffield Wednesday | – | Macclesfield Town | | 3:1 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Stafford Rangers | – | Macclesfield Town | | 3:0 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Merthyr Tydfil | – | Macclesfield Town | | 2:1 * |
| |
FA Cup 1972/73, Fourth Qualifying Round |
| | | Macclesfield Town | – | South Liverpool | | 0:1 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Macclesfield Town | – | Ellesmere Port Town | | 1:2 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Bradford City | – | Macclesfield Town | | 3:2 |
| |
FA Cup 1969/70, First Round Proper |
| 18.11.1969 | | Scunthorpe United | – | Macclesfield Town | | 4:2 (2:2) * |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Macclesfield Town | – | Lincoln City | | 1:3 |
| |
FA Cup 1967/68, Third Round Proper |
| 27.01.1968 | | Fulham | – | Macclesfield Town | | 4:2 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Nuneaton Borough | – | Macclesfield Town | | 2:0 * |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Oswestry Town | – | Macclesfield Town | | 3:2 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Macclesfield Town | – | Wrexham | | 1:2 |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Macclesfield Town | – | Frickley Colliery | | 1:3 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Droylsden | – | Macclesfield Town | | 3:2 * |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Northwich Victoria | – | Macclesfield Town | | 1:0 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Southport | – | Macclesfield Town | | 7:2 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Macclesfield Town | – | Ellesmere Port Town | | 2:3 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Macclesfield Town | – | Ellesmere Port Town | | 1:3 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Altrincham | – | Macclesfield Town | | 4:3 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Macclesfield Town | – | Hyde United | | 3:5 * |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Macclesfield Town | – | Northwich Victoria | | 0:4 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Hyde United | – | Macclesfield Town | | 3:1 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Stalybridge Celtic | – | Macclesfield Town | | 1:0 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Winsford United | – | Macclesfield Town | | 1:0 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Buxton | – | Macclesfield Town | | 2:0 * |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Altrincham | – | Macclesfield Town | | 3:1 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Macclesfield Town | – | Congleton Town | | 1:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Macclesfield Town | – | Northwich Victoria | | 0:3 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Buxton | – | Macclesfield Town | | 6:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Macclesfield Town | – | Shrewsbury Town | | 1:3 |
| |
FA Cup 1886/87, First Round |
| 13.11.1886 | | Macclesfield Town | – | Goldenhill | | 2:3 * |
| |
FA Cup 1886/87, First Round |
| 30.10.1886 | | Goldenhill | – | Macclesfield Town | | 4:2 * |
| |
FA Cup 1885/86, Second Round |
| 21.11.1885 | | Davenham | – | Macclesfield Town | | 8:1 |
| |
FA Cup 1884/85, Second Round |
| 06.12.1884 | | Macclesfield Town | – | Leek | | 1:5 |
| |
FA Cup 1883/84, First Round |
| 10.11.1883 | | Davenham | – | Macclesfield Town | | 2:0 |
| |
FA Cup 1882/83, First Round |
| 04.11.1882 | | Lockwood Brothers | – | Macclesfield Town | | 4:3 |
| |
