FA Cup 2023/24, Preliminary Round |
 | 22.08.2023 | | Leatherhead | – | South Park | | 2:1 (2:0) * |
| Leatherhead |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Leatherhead | – | Haywards Heath Town | | 3:0 (1:0) |
| Leatherhead |
FA Cup 2021/22, First Qualifying Round |
| 07.09.2021 | | Leatherhead | – | Whitstable Town | | 1:0 (1:0) * |
| Leatherhead |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Haverhill Rovers | – | Leatherhead | | 0:6 (0:2) |
| Haverhill |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Leatherhead | – | Herne Bay | | 2:0 (1:0) |
| Leatherhead |
FA Cup 2017/18, First Round Proper |
| 16.11.2017 | | Billericay Town | – | Leatherhead | | 1:3 (0:0) * |
| Billericay |
FA Cup 2017/18, Fourth Qualifying Round |
| 14.10.2017 | | Margate | – | Leatherhead | | 1:2 (0:0) |
| Margate |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Ashford Town | – | Leatherhead | | 1:2 (1:1) |
| Ashford |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Ware | – | Leatherhead | | 2:5 (2:4) |
| Ware |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Leatherhead | – | Cray Valley Paper Mills | | 6:0 (4:0) |
| Leatherhead |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Binfield | – | Leatherhead | | 1:2 |
| Binfield |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Leatherhead | – | Carshalton Athletic | | 2:1 |
| Leatherhead |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Leatherhead | – | Tooting & Mitcham United | | 1:0 |
| Leatherhead |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Leatherhead | – | Tooting & Mitcham United | | 3:1 |
| Leatherhead |
FA Cup 2012/13, Preliminary Round |
| 29.08.2012 | | Leatherhead | – | Horley Town | | 3:0 * |
| Leatherhead |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Billericay Town | – | Leatherhead | | 0:3 |
| |
FA Cup 2011/12, Second Qualifying Round |
| 04.10.2011 | | Leatherhead | – | Biggleswade Town | | 2:1 (1:0) * |
| Leatherhead |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Leatherhead | – | North Leigh | | 5:1 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Leatherhead | – | Ashford Town | | 2:0 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Leatherhead | – | Bedfont Green | | 3:0 |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | AFC Sudbury | – | Leatherhead | | 1:2 (1:1) |
| |
FA Cup 2006/07, Third Qualifying Round |
| 17.10.2006 | | Leatherhead | – | Mangotsfield United | | 4:1 * |
| |
FA Cup 2006/07, Second Qualifying Round |
| 03.10.2006 | | Leatherhead | – | Cray Wanderers | | 4:2 * |
| |
FA Cup 2006/07, First Qualifying Round |
| 19.09.2006 | | Leatherhead | – | Molesey | | 3:0 * |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Epsom & Ewell | – | Leatherhead | | 0:2 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 27.09.2005 | | Leatherhead | – | Hampton & Richmond Borough | | 2:1 * |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Chatham Town | – | Leatherhead | | 3:4 |
| |
FA Cup 2005/06, Preliminary Round |
| 30.08.2005 | | Leatherhead | – | Ash United | | 3:2 * |
| |
FA Cup 2004/05, Third Qualifying Round |
| | | Leatherhead | – | Maidstone United | | 2:1 (1:1) |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Sandhurst Town | – | Leatherhead | | 0:2 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Leatherhead | – | Cray Wanderers | | 1:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Walton & Hersham | – | Leatherhead | | 1:2 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Deal Town | – | Leatherhead | | 1:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Leatherhead | – | Moneyfields | | 3:1 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Bromley | – | Leatherhead | | 2:4 * |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Abingdon United | – | Leatherhead | | 2:3 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Banstead Athletic | – | Leatherhead | | 1:4 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Leatherhead | – | Whitehawk | | 2:0 * |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Leatherhead | – | Windsor & Eton | | 2:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Leatherhead | – | Sheppey United | | 3:1 * |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Leatherhead | – | Whitehawk | | 5:0 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Leatherhead | – | Wealdstone | | 2:0 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Milton Keynes | – | Leatherhead | | 0:4 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Leatherhead | – | Letchworth Garden City | | 8:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Langney Sports | – | Leatherhead | | 3:8 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Leatherhead | – | Corinthian-Casuals | | 3:1 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Leatherhead | – | Stowmarket Town | | 1:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Hounslow | – | Leatherhead | | 1:2 * |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Dover Athletic | – | Leatherhead | | 1:4 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Pagham | – | Leatherhead | | 0:5 |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Egham Town | – | Leatherhead | | 1:5 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Littlehampton Town | – | Leatherhead | | 0:2 |
| |
FA Cup 1980/81, Fourth Qualifying Round |
| | | Leatherhead | – | Bath City | | 1:0 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Leatherhead | – | Merthyr Tydfil | | 2:1 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Leatherhead | – | Cheshunt | | 4:1 |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Leatherhead | – | Northampton Town | | 2:0 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Chelmsford City | – | Leatherhead | | 0:4 |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Leatherhead | – | Cambridge United | | 2:0 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Leatherhead | – | Ilford | | 1:0 |
| |
FA Cup 1974/75, Third Round Proper |
| 04.01.1975 | | Brighton & Hove Albion | – | Leatherhead | | 0:1 |
| |
FA Cup 1974/75, Second Round Proper |
| 14.12.1974 | | Leatherhead | – | Colchester United | | 1:0 |
| |
FA Cup 1974/75, First Round Proper |
| 26.11.1974 | | Leatherhead | – | Bishop's Stortford | | 2:0 * |
| |
FA Cup 1974/75, Fourth Qualifying Round |
| | | Walton & Hersham | – | Leatherhead | | 1:7 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Dagenham | – | Leatherhead | | 1:3 * |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Leatherhead | – | Hornchurch | | 5:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Croydon | – | Leatherhead | | 0:2 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Leatherhead | – | Ilford | | 2:0 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Erith & Belvedere | – | Leatherhead | | 1:6 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Leatherhead | – | Worthing | | 3:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Leatherhead | – | Erith & Belvedere | | 3:0 * |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Leatherhead | – | Grays Athletic | | 3:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Tooting & Mitcham United | – | Leatherhead | | 1:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Leatherhead | – | Barking | | 3:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Leatherhead | – | Molesey | | 5:0 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Leatherhead | – | Corinthian-Casuals | | 2:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Maidenhead United | – | Leatherhead | | 0:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Leatherhead | – | Barking | | 1:0 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Chertsey Town | – | Leatherhead | | 2:5 * |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Leatherhead | – | Kingstonian | | 1:0 * |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Petter Sports | – | Leatherhead | | 0:5 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Leatherhead | – | Kingstonian | | 3:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Leatherhead | – | Cobham | | 2:0 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Vickers Armstrong | – | Leatherhead | | 1:4 |
| |
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