FA Cup 2023/24, Fourth Qualifying Round |
 | 17.10.2023 |  | Chesham United | – | Braintree Town | | 3:1 aet
(0:1, 1:1) * |
| Chesham |
FA Cup 2023/24, Third Qualifying Round |
| 30.09.2023 | | Chesham United | – | Margate | | 2:0 (1:0) |
| Chesham |
FA Cup 2023/24, Second Qualifying Round |
| 16.09.2023 | | Farnham Town | – | Chesham United | | 1:2 (0:2) |
| Farnham |
FA Cup 2023/24, First Qualifying Round |
| 02.09.2023 | | Walton & Hersham | – | Chesham United | | 1:3 (0:2) |
| Walton-on-Thames |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Chesham United | – | Peacehaven & Telscombe | | 5:2 (3:2) |
| Chesham |
FA Cup 2021/22, First Qualifying Round |
| 07.09.2021 | | Chesham United | – | Uxbridge | | 2:1 (2:1) * |
| Chesham |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Chesham United | – | Fleet Town | | 4:2 (0:0) |
| Chesham |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Chesham United | – | Biggleswade Town | | 2:1 (1:0) |
| Chesham |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Great Yarmouth Town | – | Chesham United | | 0:2 (0:0) |
| Great Yarmouth |
FA Cup 2016/17, Fourth Qualifying Round |
| 15.10.2016 | | Chesham United | – | Potters Bar Town | | 1:0 |
| Chesham |
FA Cup 2016/17, Third Qualifying Round |
| 01.10.2016 | | Chesham United | – | Staines Town | | 2:0 |
| Chesham |
FA Cup 2016/17, Second Qualifying Round |
| 20.09.2016 | | Chesham United | – | Sevenoaks Town | | 2:1 * |
| Chesham |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Chesham United | – | Saffron Walden Town | | 5:0 |
| Chesham |
FA Cup 2015/16, First Round Proper |
| 08.11.2015 | | Bristol Rovers | – | Chesham United | | 0:1 (0:0) |
| Bristol |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Chesham United | – | Enfield Town | | 2:1 (2:0) |
| Chesham |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | Chesham United | – | North Leigh | | 2:0 (0:0) |
| Chesham |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Paulton Rovers | – | Chesham United | | 0:2 (0:0) |
| Paulton |
FA Cup 2015/16, First Qualifying Round |
| 15.09.2015 | | Aylesbury | – | Chesham United | | 1:2 (0:2) * |
| Aylesbury |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Chesham United | – | Staines Lammas | | 3:2 |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Burnham Ramblers | – | Chesham United | | 0:3 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Chesham United | – | Billericay Town | | 4:2 |
| |
FA Cup 2009/10, First Qualifying Round |
| 15.09.2009 | | Harrow Borough | – | Chesham United | | 0:2 * |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Chesham United | – | Chalfont St Peter | | 2:0 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Weston-Super-Mare | – | Chesham United | | 2:4 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | North Leigh | – | Chesham United | | 2:3 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Chesham United | – | Brading Town | | 5:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Chesham United | – | Henley Town | | 5:1 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Farnborough | – | Chesham United | | 0:2 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Northampton Spencer | – | Chesham United | | 2:3 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Abingdon Town | – | Chesham United | | 1:2 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Chesham United | – | Yaxley | | 2:0 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Chalfont St Peter | – | Chesham United | | 0:6 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Chesham United | – | East Thurrock United | | 2:0 |
| |
FA Cup 2000/01, Third Qualifying Round |
| | | Stafford Rangers | – | Chesham United | | 0:2 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Chesham United | – | AFC Wallingford | | 3:2 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Bedfont | – | Chesham United | | 2:4 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Potters Bar Town | – | Chesham United | | 0:4 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Chesham United | – | Barking | | 3:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Berkhamsted Town | – | Chesham United | | 2:3 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Edgware Town | – | Chesham United | | 0:1 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Bromsgrove Rovers | – | Chesham United | | 0:1 * |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Collier Row | – | Chesham United | | 0:1 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Chesham United | – | Dagenham & Redbridge | | 2:0 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Chesham United | – | Concord Rangers | | 4:2 |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Edgware Town | – | Chesham United | | 1:2 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Chesham United | – | Chalfont St Peter | | 5:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Chesham United | – | St Albans City | | 5:0 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Chesham United | – | Berkhamsted Town | | 3:0 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Molesey | – | Chesham United | | 0:4 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Chesham United | – | Boreham Wood | | 9:1 * |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Chesham United | – | Brimsdown Rovers | | 2:1 * |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Wealdstone | – | Chesham United | | 2:4 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Chesham United | – | Wolverton | | 5:1 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Hertford Town | – | Chesham United | | 1:5 * |
| |
FA Cup 1990/91, Preliminary Round |
| | | Chesham United | – | Baldock Town | | 4:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Hornchurch | – | Chesham United | | 5:6 * |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Chesham United | – | Leyton-Wingate | | 1:0 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Chesham United | – | Wembley | | 3:2 * |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Tilbury | – | Chesham United | | 0:1 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Chelmsford City | – | Chesham United | | 1:3 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Chesham United | – | Feltham | | 1:0 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Chesham United | – | Clapton | | 3:1 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Chesham United | – | Cray Wanderers | | 3:2 |
| |
FA Cup 1979/80, Second Round Proper |
| 22.12.1979 |  | Merthyr Tydfil | – | Chesham United | | 1:3 * |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Minehead | – | Chesham United | | 1:2 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Chesham United | – | Maidstone United | | 3:1 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Bedford Town | – | Chesham United | | 0:1 * |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Chesham United | – | Haverhill Rovers | | 3:0 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Chesham United | – | Boreham Wood | | 2:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Chesham United | – | Willesden | | 5:0 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Chesham United | – | Worcester City | | 4:2 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Banbury United | – | Chesham United | | 1:4 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Thame United | – | Chesham United | | 0:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Tring Town | – | Chesham United | | 0:3 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Chesham United | – | Hornchurch | | 2:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Chesham United | – | Epping Town | | 3:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Chesham United | – | Oxford City | | 4:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Chesham United | – | Vauxhall Motors Luton | | 1:0 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Wealdstone | – | Chesham United | | 2:4 * |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Leatherhead | – | Chesham United | | 1:2 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Hemel Hempstead | – | Chesham United | | 2:3 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Chesham United | – | Southall | | 4:3 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Chesham United | – | Wembley | | 1:0 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Chesham United | – | Aylesbury United | | 5:0 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Wokingham Town | – | Chesham United | | 1:2 * |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Chesham United | – | Aylesbury United | | 5:1 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Chesham United | – | Huntley & Palmers | | 3:0 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Chesham United | – | Abingdon Town | | 5:1 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Chesham United | – | Windsor & Eton | | 2:0 * |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Chesham United | – | Banbury Spencer | | 1:0 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Chesham United | – | Banbury Spencer | | 1:0 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Chesham United | – | Marlow | | 2:0 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Chesham United | – | Huntley & Palmers | | 3:1 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Witney Town | – | Chesham United | | 1:3 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Chesham United | – | Abingdon Town | | 5:0 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Chesham United | – | Witney Town | | 4:2 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Chesham United | – | Dickinsons | | 3:0 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Chesham United | – | Hemel Hempstead | | 6:2 |
| |
FA Cup 1946/47, Extra Preliminary Round |
| | | Chesham United | – | Metal & Produce Recovery Depot | | 5:0 * |
| |
