FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 | | Hayes & Yeading United | – | Chertsey Town | | 2:1 (0:0) |
| London |
FA Cup 2023/24, Preliminary Round |
| 19.08.2023 | | Snodland Town | – | Chertsey Town | | 1:3 (1:2) |
| Snodland |
FA Cup 2022/23, Preliminary Round |
| 20.08.2022 | | Hanworth Villa | – | Chertsey Town | | 2:1 (1:0) |
| London |
FA Cup 2021/22, Fourth Qualifying Round |
| 16.10.2021 | | Southend United | – | Chertsey Town | | 4:1 (2:1) |
| Southend-on-Sea |
FA Cup 2021/22, Third qualifying round |
| 03.10.2021 | | Jersey Bulls | – | Chertsey Town | | 0:1 (0:1) |
| Saint Helier |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Chertsey Town | – | Chesham United | | 1:0 (1:0) |
| Chertsey |
FA Cup 2021/22, First Qualifying Round |
| 05.09.2021 | | Erith & Belvedere | – | Chertsey Town | | 0:4 (0:3) |
| London |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Lingfield | – | Chertsey Town | | 1:4 (0:1) |
| Whyteleafe |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Haringey Borough | – | Chertsey Town | | 2:0 |
| London |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Chertsey Town | – | Leatherhead | | 0:0,
pen. 5:4 |
| Chertsey |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Chertsey Town | – | Abbey Rangers | | 2:0 |
| Chertsey |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Maldon & Tiptree | – | Chertsey Town | | 6:1 (2:0) |
| Maldon |
FA Cup 2019/20, Second Qualifying Round |
| 22.09.2019 | | Biggleswade | – | Chertsey Town | | 1:3 (1:1) |
| Biggleswade |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Chertsey Town | – | Sheppey United | | 4:1 (1:0) |
| Chertsey |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Chertsey Town | – | Erith & Belvedere | | 5:1 (1:1) |
| Chertsey |
FA Cup 2019/20, Extra Preliminary Round |
| 13.08.2019 | | Cobham | – | Chertsey Town | | 2:4 (0:3) * |
| Cobham |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Chertsey Town | – | Cobham | | 1:1 (0:0) |
| Chertsey |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Arundel | – | Chertsey Town | | 4:1 (1:0) |
| Arundel |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Chertsey Town | – | Horsham | | 1:3 (1:1) |
| Chertsey |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Spelthorne Sports | – | Chertsey Town | | 1:3 |
| Spelthorne |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Thamesmead Town | – | Chertsey Town | | 1:0 |
| London |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Chertsey Town | – | AFC Hayes | | 3:0 |
| Chertsey |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Chertsey Town | – | Hook Norton | | 2:0 |
| Chertsey |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Chertsey Town | – | Kidlington | | 1:4 |
| Chertsey |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Reading Town | – | Chertsey Town | | 0:5 |
| Reading |
FA Cup 2014/15, Extra Preliminary Round |
| 19.08.2014 | | Milton United | – | Chertsey Town | | 1:1 aet
(1:1),
pen. 4:1 * |
| Milton |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Chertsey Town | – | Milton United | | 1:1 |
| Chertsey |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Chertsey Town | – | Chipstead | | 1:2 |
| Chertsey |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Chertsey Town | – | Highmoor Ibis | | 4:0 |
| Chertsey |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Marlow | – | Chertsey Town | | 1:2 (1:0) |
| Marlow |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Chertsey Town | – | Beckenham Town | | 1:4 |
| Chertsey |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Southend Manor | – | Chertsey Town | | 4:2 (1:0) |
| |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Chertsey Town | – | Lewes | | 4:1 |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Badshot Lea | – | Chertsey Town | | 0:1 |
| |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Chelmsford City | – | Chertsey Town | | 7:0 |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Andover | – | Chertsey Town | | 0:4 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Chertsey Town | – | Chatham Town | | 2:1 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 13.08.2010 | | Mole Valley SCR | – | Chertsey Town | | 0:5 |
| |
FA Cup 2009/10, Preliminary Round |
| 28.08.2009 | | Chertsey Town | – | Metropolitan Police | | 0:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Chessington & Hook United | – | Chertsey Town | | 0:2 |
| |
FA Cup 2008/09, Preliminary Round |
| 31.08.2008 | | Sittingbourne | – | Chertsey Town | | 2:1 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 19.08.2008 | | Deal Town | – | Chertsey Town | | 1:2 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Chertsey Town | – | Deal Town | | 2:2 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Sittingbourne | – | Chertsey Town | | 1:0 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 21.08.2007 | | Chertsey Town | – | Wick | | 3:0 * |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Wick | – | Chertsey Town | | 2:2 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Oxford City | – | Chertsey Town | | 5:0 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Chertsey Town | – | Abingdon Town | | 3:2 |
| |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Sevenoaks Town | – | Chertsey Town | | 4:2 |
| |
FA Cup 2004/05, Preliminary Round |
| | | VCD Athletic | – | Chertsey Town | | 5:1 |
| |
FA Cup 2003/04, Extra Preliminary Round |
| | | Wokingham Town | – | Chertsey Town | | 2:0 |
| |
FA Cup 2002/03, Third Qualifying Round |
| | | Molesey | – | Chertsey Town | | 3:1 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Diss Town | – | Chertsey Town | | 2:3 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Ringmer | – | Chertsey Town | | 1:2 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Chertsey Town | – | Arundel | | 4:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Chertsey Town | – | Fisher Athletic | | 0:6 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Blackfield & Langley | – | Chertsey Town | | 2:5 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Chertsey Town | – | Dartford | | 0:2 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Dartford | – | Chertsey Town | | 1:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Chertsey Town | – | Abingdon Town | | 3:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Metropolitan Police | – | Chertsey Town | | 2:1 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Oxford City | – | Chertsey Town | | 3:2 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Heybridge Swifts | – | Chertsey Town | | 2:1 * |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Chertsey Town | – | Heybridge Swifts | | 1:1 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Chertsey Town | – | Hastings Town | | 2:3 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Ringmer | – | Chertsey Town | | 1:2 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Chertsey Town | – | Tooting & Mitcham United | | 1:2 * |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Tooting & Mitcham United | – | Chertsey Town | | 2:2 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Shoreham | – | Chertsey Town | | 1:3 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Chertsey Town | – | Shoreham | | 2:2 |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Dover Athletic | – | Chertsey Town | | 1:0 * |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Chertsey Town | – | Dover Athletic | | 0:0 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Chertsey Town | – | Shoreham | | 1:0 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Sheppey United | – | Chertsey Town | | 0:1 |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Chertsey Town | – | Harrow Borough | | 1:3 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Chertsey Town | – | Tilbury | | 2:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Staines Town | – | Chertsey Town | | 1:2 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Chertsey Town | – | Kingstonian | | 1:3 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Margate | – | Chertsey Town | | 1:4 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Chertsey Town | – | Gravesend & Northfleet | | 3:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Worthing | – | Chertsey Town | | 4:1 * |
| |
FA Cup 1991/92, Preliminary Round |
| | | Chertsey Town | – | Worthing | | 2:2 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Chertsey Town | – | Walton & Hersham | | 0:3 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Basingstoke Town | – | Chertsey Town | | 3:1 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Chertsey Town | – | Eastleigh | | 4:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Chertsey Town | – | Arundel | | 3:1 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Feltham | – | Chertsey Town | | 1:0 * |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Chertsey Town | – | Feltham | | 0:0 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Chertsey Town | – | Newport IOW | | 0:1 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Chertsey Town | – | Haywards Heath | | 3:1 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Chertsey Town | – | Hendon | | 0:1 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Leytonstone/Ilford | – | Chertsey Town | | 0:1 * |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Chertsey Town | – | Leytonstone/Ilford | | 1:1 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Tring Town | – | Chertsey Town | | 1:3 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Hampton | – | Chertsey Town | | 2:0 |
| |
FA Cup 1984/85, Preliminary Round |
| | | Lancing | – | Chertsey Town | | 1:0 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Chertsey Town | – | Lancing | | 0:0 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Chertsey Town | – | Peacehaven & Telscombe | | 0:1 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Chertsey Town | – | Bromley | | 1:12 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Chertsey Town | – | Lewes | | 2:5 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Walton & Hersham | – | Chertsey Town | | 1:0 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Chertsey Town | – | Dunstable | | 2:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Chertsey Town | – | Hillingdon Borough | | 0:1 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Carshalton Athletic | – | Chertsey Town | | 3:0 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Ilford | – | Chertsey Town | | 6:1 * |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Chertsey Town | – | Ilford | | 1:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Burnham | – | Chertsey Town | | 0:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Barking | – | Chertsey Town | | 6:1 |
| |
FA Cup 1975/76, Preliminary Round |
| | | Chertsey Town | – | Gravesend & Northfleet | | 0:2 * |
| |
FA Cup 1975/76, Preliminary Round |
| | | Gravesend & Northfleet | – | Chertsey Town | | 1:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Braintree & Crittall Athletic | – | Chertsey Town | | 2:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Walton & Hersham | – | Chertsey Town | | 5:0 |
| |
FA Cup 1969/70, Preliminary Round |
| | | Chertsey Town | – | Wolverton Town & BR | | 0:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Chertsey Town | – | Walthamstow Avenue | | 1:3 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Chertsey Town | – | Leatherhead | | 2:5 * |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Leatherhead | – | Chertsey Town | | 3:3 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Walton & Hersham | – | Chertsey Town | | 4:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Chertsey Town | – | Wimbledon | | 1:3 |
| |
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