FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 |  | Hayes & Yeading United | – | Chertsey Town | | 2:1 (0:0) |
| London |
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 2020/21, Second Qualifying Round |
| 03.10.2020 | | Haringey Borough | – | Chertsey Town | | 2:0 |
| London |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Maldon & Tiptree | – | Chertsey Town | | 6:1 (2:0) |
| Maldon |
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 2016/17, First Qualifying Round |
| 03.09.2016 | | Thamesmead Town | – | Chertsey Town | | 1:0 |
| London |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Chertsey Town | – | Kidlington | | 1:4 |
| Chertsey |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Chertsey Town | – | Chipstead | | 1:2 |
| Chertsey |
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 2010/11, Second Qualifying Round |
| 25.09.2010 | | Chelmsford City | – | Chertsey Town | | 7:0 |
| |
FA Cup 2009/10, Preliminary Round |
| 28.08.2009 | | Chertsey Town | – | Metropolitan Police | | 0:1 |
| |
FA Cup 2008/09, Preliminary Round |
| 31.08.2008 | | Sittingbourne | – | Chertsey Town | | 2:1 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Sittingbourne | – | Chertsey Town | | 1:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Oxford City | – | Chertsey Town | | 5:0 |
| |
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 2001/02, First Qualifying Round |
| | | Chertsey Town | – | Fisher Athletic | | 0:6 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Chertsey Town | – | Dartford | | 0:2 * |
| |
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 1996/97, Second Qualifying Round |
| | | Chertsey Town | – | Hastings Town | | 2:3 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Chertsey Town | – | Tooting & Mitcham United | | 1:2 * |
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FA Cup 1994/95, Third Qualifying Round |
| | | Dover Athletic | – | Chertsey Town | | 1:0 * |
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FA Cup 1993/94, Third Qualifying Round |
| | | Chertsey Town | – | Harrow Borough | | 1:3 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Chertsey Town | – | Kingstonian | | 1:3 |
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FA Cup 1991/92, Preliminary Round |
| | | Worthing | – | Chertsey Town | | 4:1 * |
| |
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 1988/89, First Qualifying Round |
| | | Feltham | – | Chertsey Town | | 1:0 * |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Chertsey Town | – | Newport IOW | | 0:1 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Chertsey Town | – | Hendon | | 0:1 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Hampton | – | Chertsey Town | | 2:0 |
| |
FA Cup 1984/85, Preliminary Round |
| | | Lancing | – | Chertsey Town | | 1:0 * |
| |
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 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 1976/77, First Qualifying Round |
| | | Barking | – | Chertsey Town | | 6:1 |
| |
FA Cup 1975/76, Preliminary Round |
| | | Chertsey Town | – | Gravesend & Northfleet | | 0:2 * |
| |
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 * |
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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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