FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 | | Sittingbourne | – | Jersey Bulls | | 0:0 |
| Sittingbourne |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Fisher | – | Sittingbourne | | 2:2 (0:0) |
| London |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Sittingbourne | – | Littlehampton Town | | 2:2 (0:0) |
| Sittingbourne |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Pagham | – | Sittingbourne | | 1:1 (0:1) |
| Pagham |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Sittingbourne | – | Hythe Town | | 1:1 |
| Sittingbourne |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Metropolitan Police | – | Sittingbourne | | 0:0 |
| Molesey |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Sittingbourne | – | Horley Town | | 0:0 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Dartford | – | Sittingbourne | | 1:1 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Lymington & New Milton | – | Sittingbourne | | 1:1 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Sittingbourne | – | Slade Green | | 2:2 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Sittingbourne | – | Lewes | | 1:1 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Carshalton Athletic | – | Sittingbourne | | 2:2 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Sudbury Town | – | Sittingbourne | | 0:0 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Sittingbourne | – | Hereford United | | 2:2 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Bromley | – | Sittingbourne | | 1:1 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Erith & Belvedere | – | Sittingbourne | | 2:2 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Sittingbourne | – | Dover Athletic | | 1:1 |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Sittingbourne | – | Marlow | | 1:1 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Sittingbourne | – | Whitstable Town | | 1:1 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Rainham Town | – | Sittingbourne | | 1:1 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Sittingbourne | – | Dorking | | 1:1 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Sittingbourne | – | Staines Town | | 1:1 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Dartford | – | Sittingbourne | | 2:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Sittingbourne | – | Horsham | | 1:1 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Southall | – | Sittingbourne | | 1:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Margate | – | Sittingbourne | | 1:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Sittingbourne | – | Welling United | | 2:2 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Margate | – | Sittingbourne | | 2:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Ashford Town | – | Sittingbourne | | 0:0 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Sittingbourne | – | Ramsgate | | 1:1 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Bexhill Town | – | Sittingbourne | | 0:0 |
| |
FA Cup 1971/72, Preliminary Round |
| | | Ramsgate Athletic | – | Sittingbourne | | 1:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Sittingbourne | – | Whitstable Town | | 3:3 aet * |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Whitstable Town | – | Sittingbourne | | 1:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Deal Town | – | Sittingbourne | | 1:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Sittingbourne | – | Cray Wanderers | | 1:1 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Sittingbourne | – | Erith & Belvedere | | 3:3 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Guildford City | – | Sittingbourne | | 0:0 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Sittingbourne | – | Folkestone | | 2:2 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Sittingbourne | – | Gravesend & Northfleet | | 4:4 |
| |
FA Cup 1955/56, Third Qualifying Round |
| | | Sittingbourne | – | Ramsgate Athletic | | 1:1 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Sittingbourne | – | Carshalton Athletic | | 0:0 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Ramsgate Athletic | – | Sittingbourne | | 1:1 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Sittingbourne | – | Deal Town | | 2:2 |
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