FA Cup 2024/25, Second Qualifying Round |
 | 14.09.2024 |  | Lordswood | – | Sittingbourne | | 0:1 (0:0) |
| Chatham |
FA Cup 2024/25, First Qualifying Round |
| 03.09.2024 | | Dover Athletic | – | Sittingbourne | | 0:1 (0:1) * |
| River |
FA Cup 2024/25, Preliminary Round |
| 17.08.2024 | | Farnham Town | – | Sittingbourne | | 2:4 |
| Farnham |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Sittingbourne | – | Uxbridge | | 2:0 (0:0) |
| Sittingbourne |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Sittingbourne | – | Bearsted | | 2:0 (1:0) |
| Sittingbourne |
FA Cup 2015/16, First Qualifying Round |
| 15.09.2015 | | Sittingbourne | – | Metropolitan Police | | 1:0 (0:0) * |
| Sittingbourne |
FA Cup 2015/16, Preliminary Round |
| 28.08.2015 | | Seven Acre & Sidcup | – | Sittingbourne | | 1:2 |
| London |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Thamesmead Town | – | Sittingbourne | | 1:2 |
| London |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Sittingbourne | – | Littlehampton Town | | 3:2 |
| Sittingbourne |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Chessington & Hook United | – | Sittingbourne | | 0:1 |
| London |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Sittingbourne | – | Burnham | | 2:1 |
| Sittingbourne |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Sittingbourne | – | Peacehaven & Telscombe | | 2:1 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Folkestone Invicta | – | Sittingbourne | | 0:1 |
| |
FA Cup 2009/10, Preliminary Round |
| 01.09.2009 | | Horley Town | – | Sittingbourne | | 0:2 * |
| |
FA Cup 2008/09, Preliminary Round |
| 31.08.2008 | | Sittingbourne | – | Chertsey Town | | 2:1 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Sittingbourne | – | Chertsey Town | | 1:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Sittingbourne | – | Hassocks | | 3:0 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Sittingbourne | – | Thamesmead Town | | 3:1 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Sittingbourne | – | Whyteleafe | | 1:0 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Sidlesham | – | Sittingbourne | | 0:2 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Wokingham Town | – | Sittingbourne | | 0:4 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Sittingbourne | – | Godalming & Guildford | | 2:0 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Hailsham Town | – | Sittingbourne | | 1:3 |
| |
FA Cup 1999/00, Preliminary Round |
| | | East Cowes Victoria | – | Sittingbourne | | 0:1 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Portfield | – | Sittingbourne | | 1:2 |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Sittingbourne | – | Langney Sports | | 2:1 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Sittingbourne | – | Purfleet | | 2:1 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Sittingbourne | – | Molesey | | 5:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Horsham YMCA | – | Sittingbourne | | 2:3 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Sittingbourne | – | Bromley | | 3:2 * |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Sittingbourne | – | Erith & Belvedere | | 6:1 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Horsham | – | Sittingbourne | | 0:5 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Dover Athletic | – | Sittingbourne | | 1:2 * |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Sittingbourne | – | Havant Town | | 3:2 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Sittingbourne | – | Fareham Town | | 3:2 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Whitehawk | – | Sittingbourne | | 0:1 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Whitstable Town | – | Sittingbourne | | 1:2 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Southwick | – | Sittingbourne | | 1:3 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Whitstable Town | – | Sittingbourne | | 1:4 * |
| |
FA Cup 1990/91, Preliminary Round |
| | | Sittingbourne | – | Burgess Hill Town | | 2:0 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Haywards Heath | – | Sittingbourne | | 0:3 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Thanet United | – | Sittingbourne | | 2:3 |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Sittingbourne | – | Three Bridges | | 3:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Horsham | – | Sittingbourne | | 1:2 * |
| |
FA Cup 1983/84, Preliminary Round |
| | | Sittingbourne | – | Ringmer | | 3:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Metropolitan Police | – | Sittingbourne | | 1:2 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Hastings United | – | Sittingbourne | | 3:5 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Sittingbourne | – | Bexhill Town | | 1:0 * |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Sittingbourne | – | Whitstable Town | | 2:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Chatham Town | – | Sittingbourne | | 1:6 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Sittingbourne | – | Deal Town | | 6:2 * |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Bromley | – | Sittingbourne | | 0:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Sittingbourne | – | Faversham Town | | 9:0 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Cray Wanderers | – | Sittingbourne | | 0:1 * |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Erith & Belvedere | – | Sittingbourne | | 1:2 * |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Sittingbourne | – | Guildford City | | 1:0 * |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Sittingbourne | – | Dover | | 2:1 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Folkestone | – | Sittingbourne | | 1:2 * |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Sittingbourne | – | Whitstable | | 10:0 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Sheppey United | – | Sittingbourne | | 1:4 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Tonbridge | – | Sittingbourne | | 0:2 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Erith & Belvedere | – | Sittingbourne | | 0:4 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Sheppey United | – | Sittingbourne | | 2:5 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Sittingbourne | – | Gravesend & Northfleet | | 1:0 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Ramsgate Athletic | – | Sittingbourne | | 1:2 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Deal Town | – | Sittingbourne | | 3:5 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Carshalton Athletic | – | Sittingbourne | | 1:2 * |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Sittingbourne | – | Tunbridge Wells United | | 2:0 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Sittingbourne | – | Bexleyheath & Welling | | 4:2 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Sittingbourne | – | Snowdown Colliery Welfare | | 2:1 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Sittingbourne | – | Tooting & Mitcham United | | 2:1 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Sittingbourne | – | Ramsgate Athletic | | 2:1 * |
| |
FA Cup 1953/54, Preliminary Round |
| | | Sittingbourne | – | Carshalton Athletic | | 2:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Tunbridge Wells United | – | Sittingbourne | | 2:4 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Sittingbourne | – | Faversham Town | | 3:1 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Deal Town | – | Sittingbourne | | 1:3 * |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Sittingbourne | – | Maidstone United | | 2:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Canterbury City | – | Sittingbourne | | 0:1 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Sittingbourne | – | Southall | | 2:1 |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Chatham | – | Sittingbourne | | 0:3 |
| |
