FA Cup 2023/24, Extra Preliminary Round |
 | 08.08.2023 | | Jersey Bulls | – | Sittingbourne | | 2:0 (0:0) * |
| Sittingbourne |
FA Cup 2022/23, Preliminary Round |
| 23.08.2022 | | Sittingbourne | – | Fisher | | 0:1 (0:1) * |
| Sittingbourne |
FA Cup 2021/22, Preliminary Round |
| 25.08.2021 | | Littlehampton Town | – | Sittingbourne | | 4:0 (2:0) * |
| Littlehampton |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Deal Town | – | Sittingbourne | | 4:1 |
| Deal |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Bognor Regis Town | – | Sittingbourne | | 3:0 (3:0) |
| Bognor Regis |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Sittingbourne | – | Gosport Borough | | 0:1 (0:0) |
| Sittingbourne |
FA Cup 2017/18, Preliminary Round |
| 22.08.2017 | | Sittingbourne | – | Pagham | | 0:1 (0:0) * |
| Sittingbourne |
FA Cup 2016/17, Preliminary Round |
| 23.08.2016 | | Hythe Town | – | Sittingbourne | | 5:0 * |
| Hythe |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Sittingbourne | – | Hoddesdon Town | | 1:2 (0:1) |
| Sittingbourne |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Sittingbourne | – | Dorking Wanderers | | 0:3 |
| Sittingbourne |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Staines Town | – | Sittingbourne | | 4:1 (2:1) |
| Staines |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Whitehawk | – | Sittingbourne | | 5:0 |
| Whitehawk |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Bognor Regis Town | – | Sittingbourne | | 1:0 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Sittingbourne | – | Andover | | 0:1 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Sittingbourne | – | Staines Town | | 2:3 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Erith & Belvedere | – | Sittingbourne | | 2:0 |
| |
FA Cup 2007/08, First Qualifying Round |
| 18.09.2007 | | Sittingbourne | – | Dartford | | 1:5 * |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Fisher Athletic | – | Sittingbourne | | 7:1 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Sittingbourne | – | Chessington & Hook United | | 2:4 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Sittingbourne | – | Lymington & New Milton | | 1:2 * |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Sittingbourne | – | East Thurrock United | | 1:2 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Slade Green | – | Sittingbourne | | 3:1 * |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Lewes | – | Sittingbourne | | 6:3 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Sittingbourne | – | Horsham | | 0:3 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Sittingbourne | – | Carshalton Athletic | | 0:1 * |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Sittingbourne | – | Sudbury Town | | 1:2 * |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Hereford United | – | Sittingbourne | | 3:0 * |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Sittingbourne | – | Tooting & Mitcham United | | 4:5 |
| |
FA Cup 1995/96, Fourth Qualifying Round |
| | | Sittingbourne | – | Dorchester Town | | 1:2 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Folkestone Invicta | – | Sittingbourne | | 1:0 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Sittingbourne | – | Gravesend & Northfleet | | 0:2 |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Marlow | – | Sittingbourne | | 2:1 * |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Sittingbourne | – | Tonbridge | | 1:2 |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Dover Athletic | – | Sittingbourne | | 2:0 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Whyteleafe | – | Sittingbourne | | 1:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Sittingbourne | – | Hastings Town | | 2:3 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Sittingbourne | – | Rainham Town | | 2:3 * |
| |
FA Cup 1986/87, Preliminary Round |
| | | Dorking | – | Sittingbourne | | 2:1 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Sittingbourne | – | Banstead Athletic | | 1:2 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Staines Town | – | Sittingbourne | | 3:0 * |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Sittingbourne | – | Dartford | | 1:4 * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Sittingbourne | – | Southall | | 1:3 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Finchley | – | Sittingbourne | | 4:3 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Sittingbourne | – | Margate | | 3:4 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Welling United | – | Sittingbourne | | 5:0 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Sittingbourne | – | Eastbourne United | | 1:4 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Sittingbourne | – | Haywards Heath | | 0:2 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Sittingbourne | – | Margate | | 0:1 * |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Ramsgate | – | Sittingbourne | | 4:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Sittingbourne | – | Ashford Town | | 1:2 * |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Ramsgate | – | Sittingbourne | | 2:0 * |
| |
FA Cup 1972/73, Third Qualifying Round |
| | | Tonbridge | – | Sittingbourne | | 4:1 |
| |
FA Cup 1971/72, Preliminary Round |
| | | Sittingbourne | – | Ramsgate Athletic | | 0:1 * |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Sittingbourne | – | Maidstone United | | 0:5 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Sittingbourne | – | Tunbridge Wells | | 0:1 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Canterbury City | – | Sittingbourne | | 2:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Whitstable Town | – | Sittingbourne | | 3:2 * |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Sittingbourne | – | Ramsgate Athletic | | 1:3 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Bexley United | – | Sittingbourne | | 4:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Sittingbourne | – | Bexley United | | 0:3 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Sittingbourne | – | Bexley United | | 0:2 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Hinckley Athletic | – | Sittingbourne | | 3:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Dartford | – | Sittingbourne | | 5:0 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Bexleyheath & Welling | – | Sittingbourne | | 1:0 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Bexleyheath & Welling | – | Sittingbourne | | 5:1 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Gravesend & Northfleet | – | Sittingbourne | | 2:0 * |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Gravesend & Northfleet | – | Sittingbourne | | 3:1 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Sittingbourne | – | Margate | | 2:3 |
| |
FA Cup 1955/56, Third Qualifying Round |
| | | Ramsgate Athletic | – | Sittingbourne | | 3:2 * |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Canterbury City | – | Sittingbourne | | 2:1 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Guildford City | – | Sittingbourne | | 2:0 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Gravesend & Northfleet | – | Sittingbourne | | 3:0 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Snowdown Colliery Welfare | – | Sittingbourne | | 4:2 |
| |
FA Cup 1950/51, Second Qualifying Round |
| | | Tonbridge | – | Sittingbourne | | 3:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Sittingbourne | – | Erith & Belvedere | | 0:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Gravesend & Northfleet | – | Sittingbourne | | 3:1 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Sittingbourne | – | Bexley | | 3:4 |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Folkestone | – | Sittingbourne | | 5:3 |
| |
FA Cup 1928/29, Second Round Proper |
| 08.12.1928 | | Walsall | – | Sittingbourne | | 2:1 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Sittingbourne | – | Northfleet United | | 1:3 |
| |
FA Cup 1925/26, Second Round Proper |
| 12.12.1925 | | Swindon Town | – | Sittingbourne | | 7:0 |
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