FA Cup 2022/23, Extra Preliminary Round |
 | 10.08.2022 |  | Newhaven | – | Canterbury City | | 10:0 (6:0) * |
| Lancing |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Balham | – | Canterbury City | | 3:0 (1:0) |
| London |
FA Cup 2020/21, Extra Preliminary Round |
| 02.09.2020 | | Guildford City | – | Canterbury City | | 3:2 |
| Guildford |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | South Park | – | Canterbury City | | 2:1 (0:1) |
| Reigate |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Corinthian | – | Canterbury City | | 3:0 (1:0) |
| Hartley Gay Dawn Farm |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Sutton Common Rovers | – | Canterbury City | | 2:0 |
| Sutton |
FA Cup 2016/17, Preliminary Round |
| 24.08.2016 | | Pagham | – | Canterbury City | | 2:1 aet
(1:1) * |
| Pagham |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Dorking Wanderers | – | Canterbury City | | 6:2 |
| Dorking |
FA Cup 2014/15, Preliminary Round |
| 31.08.2014 | | Canterbury City | – | Pagham | | 0:2 |
| Herne Bay |
FA Cup 2013/14, Extra Preliminary Round |
| 18.08.2013 | | Dorking Wanderers | – | Canterbury City | | 5:0 |
| Dorking |
FA Cup 1999/00, Preliminary Round |
| | | Herne Bay | – | Canterbury City | | 1:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Crawley Town | – | Canterbury City | | 5:0 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Worthing | – | Canterbury City | | 4:1 * |
| |
FA Cup 1996/97, Preliminary Round |
| | | Arundel | – | Canterbury City | | 3:0 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Raynes Park Vale | – | Canterbury City | | 3:0 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Canterbury City | – | Peacehaven & Telscombe | | 1:2 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Canterbury City | – | Chatham Town | | 1:4 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Worthing | – | Canterbury City | | 3:1 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Gravesend & Northfleet | – | Canterbury City | | 2:1 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Dorking | – | Canterbury City | | 4:1 * |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Canterbury City | – | Dover Athletic | | 0:2 * |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Woking | – | Canterbury City | | 3:0 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Thanet United | – | Canterbury City | | 3:0 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Canterbury City | – | Folkestone | | 0:1 |
| |
FA Cup 1985/86, Third Qualifying Round |
| | | Hastings Town | – | Canterbury City | | 3:0 |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Canterbury City | – | Enfield | | 0:1 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Canterbury City | – | Bognor Regis Town | | 0:3 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Tooting & Mitcham United | – | Canterbury City | | 2:0 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Hastings United | – | Canterbury City | | 4:1 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Canterbury City | – | Dover | | 0:2 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Dulwich Hamlet | – | Canterbury City | | 4:0 * |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Ramsgate | – | Canterbury City | | 1:0 |
| |
FA Cup 1977/78, Preliminary Round |
| | | Tunbridge Wells | – | Canterbury City | | 5:0 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Ashford Town | – | Canterbury City | | 1:0 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Hendon | – | Canterbury City | | 1:0 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Ashford Town | – | Canterbury City | | 4:0 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Maidstone United | – | Canterbury City | | 4:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Cray Wanderers | – | Canterbury City | | 2:1 |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Canterbury City | – | Folkestone | | 1:3 |
| |
FA Cup 1970/71, Preliminary Round |
| | | Hastings United | – | Canterbury City | | 2:0 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Canterbury City | – | Ashford Town | | 1:4 * |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Swindon Town | – | Canterbury City | | 1:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Canterbury City | – | Tonbridge | | 1:2 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Hastings United | – | Canterbury City | | 2:0 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Folkestone | – | Canterbury City | | 1:0 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Canterbury City | – | Torquay United | | 0:6 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Canterbury City | – | Ramsgate Athletic | | 0:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Canterbury City | – | Folkestone | | 0:3 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Ramsgate Athletic | – | Canterbury City | | 2:1 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Dover | – | Canterbury City | | 4:1 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Betteshanger Colliery Welfare | – | Canterbury City | | 6:0 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Canterbury City | – | Ashford Town | | 2:4 * |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Canterbury City | – | Whitstable | | 1:5 * |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Margate | – | Canterbury City | | 2:0 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Canterbury City | – | Ramsgate Athletic | | 2:5 * |
| |
FA Cup 1954/55, Fourth Qualifying Round |
| | | Hounslow Town | – | Canterbury City | | 3:0 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Canterbury City | – | Tunbridge Wells United | | 0:2 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Tunbridge Wells United | – | Canterbury City | | 2:1 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Margate | – | Canterbury City | | 6:1 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Canterbury City | – | Sittingbourne | | 0:1 |
| |
FA Cup 1949/50, Second Qualifying Round |
| | | Gravesend & Northfleet | – | Canterbury City | | 5:1 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Margate | – | Canterbury City | | 3:1 |
| |
