FA Cup 2023/24, First Qualifying Round |
 | 05.09.2023 |  | Horsham | – | Leatherhead | | 2:1 (1:1) * |
| Horsham |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Leatherhead | – | Chichester City | | 1:2 (1:1) |
| Leatherhead |
FA Cup 2021/22, Second qualifying round |
| 21.09.2021 | | Corinthian-Casuals | – | Leatherhead | | 3:0 (1:0) * |
| London |
FA Cup 2018/19, Fourth Qualifying Round |
| 24.10.2018 | | Leatherhead | – | Hitchin Town | | 1:2 aet
(1:0, 1:1) * |
| Leatherhead |
FA Cup 2017/18, Second Round Proper |
| 03.12.2017 | | Wycombe Wanderers | – | Leatherhead | | 3:1 (1:1) |
| High Wycombe |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Hythe Town | – | Leatherhead | | 1:0 |
| Hythe |
FA Cup 2015/16, First Qualifying Round |
| 23.09.2015 | | Leatherhead | – | South Park | | 1:3 (0:2) * |
| Leatherhead |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Leatherhead | – | Faversham Town | | 1:2 |
| Leatherhead |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Biggleswade Town | – | Leatherhead | | 5:1 (1:0) |
| Biggleswade |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Chelmsford City | – | Leatherhead | | 2:1 |
| Chelmsford |
FA Cup 2011/12, Fourth Qualifying Round |
| 01.11.2011 | | Leatherhead | – | Sutton United | | 2:3 aet
(1:1, 2:2) * |
| Leatherhead |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Leatherhead | – | Burgess Hill Town | | 0:2 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 29.09.2009 | | Leatherhead | – | Lewes | | 0:1 * |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Ashford Town | – | Leatherhead | | 3:2 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Dartford | – | Leatherhead | | 3:0 |
| |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Torquay United | – | Leatherhead | | 2:1 (0:1) |
| Torquay |
FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Leatherhead | – | Farnborough Town | | 0:2 |
| |
FA Cup 2004/05, Fourth Qualifying Round |
| | | Bath City | – | Leatherhead | | 1:0 (1:0) |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Leyton | – | Leatherhead | | 1:0 |
| |
FA Cup 2002/03, Third Qualifying Round |
| | | Leatherhead | – | Ford United | | 1:2 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Oxford City | – | Leatherhead | | 2:0 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Metropolitan Police | – | Leatherhead | | 2:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Leatherhead | – | Cowes Sports | | 0:1 |
| |
FA Cup 1998/99, Fourth Qualifying Round |
| | | Rushden & Diamonds | – | Leatherhead | | 4:0 * |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Langney Sports | – | Leatherhead | | 2:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Tonbridge | – | Leatherhead | | 1:0 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Harrow Borough | – | Leatherhead | | 2:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Hayes | – | Leatherhead | | 4:0 * |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Leatherhead | – | Metropolitan Police | | 3:5 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Lewes | – | Leatherhead | | 1:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Leatherhead | – | Dorking | | 1:2 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Ashford Town | – | Leatherhead | | 3:1 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Folkestone | – | Leatherhead | | 2:1 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Barnet | – | Leatherhead | | 4:3 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Darenth Heathside | – | Leatherhead | | 2:1 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Eastbourne Town | – | Leatherhead | | 3:1 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Leatherhead | – | Redhill | | 0:2 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Leatherhead | – | Hastings United | | 1:2 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Leatherhead | – | Fisher Athletic | | 0:4 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Wokingham Town | – | Leatherhead | | 1:0 |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Leatherhead | – | Dover | | 0:1 * |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Exeter City | – | Leatherhead | | 5:0 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Croydon | – | Leatherhead | | 3:0 * |
| |
FA Cup 1978/79, Second Round Proper |
| 19.12.1978 | | Colchester United | – | Leatherhead | | 4:0 * |
| |
FA Cup 1977/78, First Round Proper |
| 29.11.1977 |  | Swansea City | – | Leatherhead | | 2:1 * |
| |
FA Cup 1976/77, Second Round Proper |
| 14.12.1976 | | Leatherhead | – | Wimbledon | | 1:3 |
| |
FA Cup 1975/76, Second Round Proper |
| 22.12.1975 | | Tooting & Mitcham United | – | Leatherhead | | 2:1 * |
| |
FA Cup 1974/75, Fourth Round Proper |
| 25.01.1975 | | Leicester City | – | Leatherhead | | 3:2 |
| Leicester |
FA Cup 1973/74, Third Qualifying Round |
| | | Leytonstone | – | Leatherhead | | 1:0 * |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Bognor Regis Town | – | Leatherhead | | 2:0 |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Bexley United | – | Leatherhead | | 3:2 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Leatherhead | – | Wimbledon | | 1:2 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Leatherhead | – | Walton & Hersham | | 0:1 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Walton & Hersham | – | Leatherhead | | 4:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Clapton | – | Leatherhead | | 2:1 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Leatherhead | – | Chesham United | | 1:2 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Guildford City | – | Leatherhead | | 3:0 * |
| |
FA Cup 1964/65, Third Qualifying Round |
| | | Leatherhead | – | Guildford City | | 1:2 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Guildford City | – | Leatherhead | | 5:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Leatherhead | – | Wimbledon | | 1:4 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Kingstonian | – | Leatherhead | | 4:2 * |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Leatherhead | – | Dorking | | 1:2 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Sutton United | – | Leatherhead | | 6:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Leatherhead | – | Walton & Hersham | | 1:3 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Leatherhead | – | Hounslow Town | | 2:6 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Leatherhead | – | Sutton United | | 0:2 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Woking | – | Leatherhead | | 2:0 |
| |
