FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Braintree Town | – | Chesham United | | 0:0 |
| Braintree |
FA Cup 2022/23, Second Qualifying Round |
| 16.09.2022 | | Chesham United | – | Bracknell Town | | 2:2 (0:0) |
| Chesham |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Uxbridge | – | Chesham United | | 2:2 (1:2) |
| London |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Hastings United | – | Chesham United | | 0:0,
pen. 6:5 |
| Hastings |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Sevenoaks Town | – | Chesham United | | 2:2 |
| Sevenoaks |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Chesham United | – | Aylesbury | | 0:0 |
| Chesham |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Dunstable Town | – | Chesham United | | 2:2 (2:1) |
| Dunstable |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Chesham United | – | Wealdstone | | 2:2 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Chesham United | – | Harrow Borough | | 1:1 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Chesham United | – | Stotfold | | 1:1 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Chesham United | – | Bedford Town | | 1:1 |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Weston-Super-Mare | – | Chesham United | | 1:1 (1:0) |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Chesham United | – | Bromsgrove Rovers | | 1:1 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Boreham Wood | – | Chesham United | | 2:2 |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Aylesbury United | – | Chesham United | | 1:1 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Brimsdown Rovers | – | Chesham United | | 2:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Chesham United | – | Hertford Town | | 0:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Aveley | – | Chesham United | | 0:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Chesham United | – | Hornchurch | | 1:1 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Heybridge Swifts | – | Chesham United | | 0:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Leyton-Wingate | – | Chesham United | | 2:2 |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Wembley | – | Chesham United | | 0:0 |
| |
FA Cup 1979/80, Second Round Proper |
| 19.12.1979 | | Chesham United | – | Merthyr Tydfil |  | 1:1 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Chesham United | – | Bedford Town | | 0:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Haverhill Rovers | – | Chesham United | | 0:0 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Chesham United | – | Berkhamsted Town | | 3:3 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Chesham United | – | Finchley | | 0:0 aet * |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Finchley | – | Chesham United | | 2:2 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Chesham United | – | Wealdstone | | 1:1 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Chesham United | – | Hemel Hempstead | | 1:1 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Chesham United | – | Wokingham Town | | 2:2 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Chesham United | – | Marlow | | 2:2 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Windsor & Eton | – | Chesham United | | 2:2 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Chesham United | – | Maidenhead United | | 5:5 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Chesham United | – | Wycombe Wanderers | | 1:1 |
| |
FA Cup 1946/47, Extra Preliminary Round |
| | | Metal & Produce Recovery Depot | – | Chesham United | | 1:1 |
| |
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