FA Cup 2022/23, First Qualifying Round |
 | 03.09.2022 | | Midhurst & Easebourne | – | Chatham Town | | 0:6 (0:5) |
| Midhurst |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Colliers Wood United | – | Chatham Town | | 0:2 (0:1) |
| Colliers Wood |
FA Cup 2022/23, Extra Preliminary Round |
| 07.08.2022 | | Little Common | – | Chatham Town | | 1:2 (0:1) |
| Bexhill-on-Sea |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Chatham Town | – | Eastbourne United | | 6:2 (3:1) |
| Chatham |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Folkestone Invicta | – | Chatham Town | | 0:3 |
| Folkestone |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Chatham Town | – | Southall | | 3:2 |
| Chatham |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Westside | – | Chatham Town | | 0:2 |
| London |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | East Preston | – | Chatham Town | | 0:2 |
| East Preston |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Chatham Town | – | Walton & Hersham | | 3:1 (1:0) |
| Chatham |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Chatham Town | – | Cray Wanderers | | 1:0 (1:0) |
| Chatham |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Chichester City | – | Chatham Town | | 0:4 |
| Chichester |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Horsham | – | Chatham Town | | 0:1 (0:0) |
| Horsham |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Whyteleafe | – | Chatham Town | | 1:2 |
| Whyteleafe |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Chatham Town | – | East Preston | | 2:1 |
| Chatham |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Erith & Belvedere | – | Chatham Town | | 0:5 |
| London |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Chatham Town | – | Peacehaven & Telscombe | | 2:1 |
| Chatham |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Chatham Town | – | Croydon Athletic | | 1:0 |
| |
FA Cup 2009/10, Preliminary Round |
| 01.09.2009 | | Eastbourne United Association | – | Chatham Town | | 1:2 * |
| |
FA Cup 2008/09, Preliminary Round |
| 02.09.2008 | | Dorking | – | Chatham Town | | 0:1 * |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Ringmer | – | Chatham Town | | 1:4 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Chatham Town | – | North Leigh | | 2:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Reading Town | – | Chatham Town | | 2:3 * |
| |
FA Cup 2002/03, Preliminary Round |
| | | Egham Town | – | Chatham Town | | 0:1 * |
| |
FA Cup 2000/01, Preliminary Round |
| | | Chatham Town | – | Molesey | | 3:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Ash United | – | Chatham Town | | 1:2 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Chatham Town | – | Whyteleafe | | 2:0 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Ramsgate | – | Chatham Town | | 0:2 * |
| |
FA Cup 1995/96, Preliminary Round |
| | | Chatham Town | – | Whyteleafe | | 3:1 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Canterbury City | – | Chatham Town | | 1:4 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Burgess Hill Town | – | Chatham Town | | 0:1 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Arundel | – | Chatham Town | | 2:3 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Crawley Town | – | Chatham Town | | 1:3 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Chatham Town | – | Collier Row | | 4:1 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Vauxhall Motors Luton | – | Chatham Town | | 0:2 * |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Chatham Town | – | Southall | | 4:2 * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Hastings Town | – | Chatham Town | | 2:7 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Chatham Town | – | Woking | | 2:1 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Chatham Town | – | Tonbridge | | 1:0 * |
| |
FA Cup 1980/81, Preliminary Round |
| | | Chatham Town | – | Eastbourne United | | 2:1 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Dover | – | Chatham Town | | 0:1 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Horsham | – | Chatham Town | | 1:2 * |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Medway | – | Sidley United | | 4:1 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Medway | – | Faversham Town | | 2:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Medway | – | Whitstable Town | | 4:2 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Fleet Town | – | Chatham Town | | 2:4 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Chatham Town | – | Molesey | | 3:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Chatham Town | – | Maidstone United | | 4:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Chatham Town | – | Bromley | | 3:1 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Lloyds | – | Chatham Town | | 2:4 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Chatham | – | St Albans City | | 3:1 |
| |
FA Cup 1888/89, Second Round Proper |
| 28.02.1889 | | Chatham | – | Nottingham Forest | | 3:2 * |
| London |
FA Cup 1888/89, First Round Proper |
| 02.02.1889 | | Chatham | – | South Shore | | 2:1 |
| |
FA Cup 1887/88, Second Round |
| 05.11.1887 | | Chatham | – | Royal Engineers | | 3:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Chatham | – | Luton Town | | 5:1 |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Chatham | – | Hotspur | | 1:0 |
| |
FA Cup 1884/85, Fourth Round |
| 24.01.1885 | | Chatham | – | Lower Darwen | | 1:0 |
| |
FA Cup 1884/85, Third Round |
| 03.01.1885 | | Hanover United | – | Chatham | | 0:2 |
| |
FA Cup 1884/85, Second Round |
| 06.12.1884 | | Chatham | – | Hendon | | 1:0 |
| |
FA Cup 1886/87, First Round |
| | | Chatham | – | Bournemouth Rovers | | +:- |
| |
FA Cup 1884/85, First Round |
| | | Chatham | – | Windsor Home Park | | +:- |
| |
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