FA Cup 2023/24, Second Qualifying Round |
 | 20.09.2023 |  | Ramsgate | – | Cray Wanderers | | 3:2 aet
(1:0, 2:2) * |
| Ramsgate |
FA Cup 2022/23, First Qualifying Round |
| 07.09.2022 | | Cray Wanderers | – | Bognor Regis Town | | 0:4 (0:2) * |
| London |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Cray Wanderers | – | Sutton Common Rovers | | 1:3 (1:2) |
| London |
FA Cup 2020/21, Fourth Qualifying Round |
| 24.10.2020 | | Canvey Island | – | Cray Wanderers | | 3:2 |
| Canvey Island |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Haringey Borough | – | Cray Wanderers | | 1:0 (0:0) |
| London |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Metropolitan Police | – | Cray Wanderers | | 3:2 (1:2) |
| Molesey |
FA Cup 2017/18, Preliminary Round |
| 20.08.2017 | | Cray Wanderers | – | Sevenoaks Town | | 2:3 (0:2) |
| London |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Faversham Town | – | Cray Wanderers | | 1:0 |
| Faversham |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Chatham Town | – | Cray Wanderers | | 1:0 (1:0) |
| Chatham |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Cray Wanderers | – | Tooting & Mitcham United | | 1:2 (0:1) |
| London |
FA Cup 2013/14, First Qualifying Round |
| 15.09.2013 | | Cray Wanderers | – | Faversham Town | | 0:3 (0:0) |
| London |
FA Cup 2012/13, Third Qualifying Round |
| 06.10.2012 | | Cray Wanderers | – | Chelmsford City | | 1:2 (1:0) |
| London |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Cray Wanderers | – | Dartford | | 1:2 |
| |
FA Cup 2010/11, Second Qualifying Round |
| 28.09.2010 | | Ebbsfleet United | – | Cray Wanderers | | 4:2 * |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Walton & Hersham | – | Cray Wanderers | | 2:1 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Sutton United | – | Cray Wanderers | | 3:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 16.09.2007 | | Cray Wanderers | – | AFC Wimbledon | | 2:6 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 03.10.2006 | | Leatherhead | – | Cray Wanderers | | 4:2 * |
| |
FA Cup 2005/06, Fourth Qualifying Round |
| 22.10.2005 | | Grays Athletic | – | Cray Wanderers | | 2:0 (1:0) |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Leatherhead | – | Cray Wanderers | | 1:0 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Basingstoke Town | – | Cray Wanderers | | 1:0 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Hemel Hempstead Town | – | Cray Wanderers | | 3:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Bracknell Town | – | Cray Wanderers | | 3:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Cowes Sports | – | Cray Wanderers | | 1:0 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Horsham YMCA | – | Cray Wanderers | | 3:0 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Cray Wanderers | – | Ruislip Manor | | 2:3 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Baldock Town | – | Cray Wanderers | | 3:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Cray Wanderers | – | Tilbury | | 1:4 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Burnham | – | Cray Wanderers | | 2:1 * |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Kingstonian | – | Cray Wanderers | | 2:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Canterbury City | – | Cray Wanderers | | 5:0 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Bromley | – | Cray Wanderers | | 4:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Addlestone & Weybridge Town | – | Cray Wanderers | | 3:1 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Chesham United | – | Cray Wanderers | | 3:2 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Cray Wanderers | – | Billericay Town | | 0:4 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Tilbury | – | Cray Wanderers | | 4:1 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Kingstonian | – | Cray Wanderers | | 1:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Cray Wanderers | – | Dulwich Hamlet | | 1:2 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Snowdown Colliery Welfare | – | Cray Wanderers | | 2:1 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Cray Wanderers | – | Bromley | | 0:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Cray Wanderers | – | Dulwich Hamlet | | 1:3 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Cray Wanderers | – | Sutton United | | 1:5 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Cray Wanderers | – | Hampton | | 1:3 * |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Cray Wanderers | – | Dover | | 0:2 |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Braintree & Crittall Athletic | – | Cray Wanderers | | 1:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Ilford | – | Cray Wanderers | | 3:0 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Dagenham | – | Cray Wanderers | | 3:0 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Redhill | – | Cray Wanderers | | 1:0 |
| |
FA Cup 1967/68, Third Qualifying Round |
| | | Dagenham | – | Cray Wanderers | | 1:0 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Cray Wanderers | – | Barnet | | 1:4 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Cray Wanderers | – | Sheppey United | | 0:1 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Dartford | – | Cray Wanderers | | 5:0 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Cray Wanderers | – | Sittingbourne | | 0:1 * |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Sutton United | – | Cray Wanderers | | 4:1 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Cray Wanderers | – | Erith & Belvedere | | 3:4 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Cray Wanderers | – | Dartford | | 4:5 |
| |
