FA Cup 2023/24, Preliminary Round |
 | 19.08.2023 | | Boldmere St Michaels | – | Chasetown | | 1:0 (1:0) |
| Sutton Coldfield |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | St Ives Town | – | Chasetown | | 3:1 (1:1) |
| St Ives |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Hanley Town | – | Chasetown | | 2:1 (0:0) |
| Hanley |
FA Cup 2019/20, Second Qualifying Round |
| 24.09.2019 | | Chasetown | – | Leamington | | 1:2 aet
(1:0, 1:1) * |
| Chasetown |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Gainsborough Trinity | – | Chasetown | | 8:2 (3:0) * |
| Gainsborough |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Buxton | – | Chasetown | | 4:1 (3:1) |
| Buxton |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Chasetown | – | Bedworth United | | 0:1 |
| Chasetown |
FA Cup 2015/16, Third Qualifying Round |
| 13.10.2015 | | Stalybridge Celtic | – | Chasetown | | 2:0 (1:0) * |
| Stalybridge |
FA Cup 2014/15, First Qualifying Round |
| 16.09.2014 | | Chasetown | – | Rugby Town | | 1:3 aet
(1:1, 1:1) * |
| Chasetown |
FA Cup 2013/14, First Qualifying Round |
| 17.09.2013 | | Stafford Rangers | – | Chasetown | | 2:0 (1:0) * |
| Stafford |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Dereham Town | – | Chasetown | | 2:1 (1:0) |
| Dereham |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Chasetown | – | Grantham Town | | 1:2 (0:1) |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Kidsgrove Athletic | – | Chasetown | | 3:0 |
| |
FA Cup 2008/09, Third Qualifying Round |
| 11.10.2008 | | Evesham United | – | Chasetown | | 2:0 (0:0) |
| |
FA Cup 2007/08, Third Round Proper |
| 05.01.2008 | | Chasetown | – | Cardiff City | | 1:3 (1:1) |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Halesowen Town | – | Chasetown | | 3:1 |
| |
FA Cup 2005/06, First Round Proper |
| 16.11.2005 | | Oldham Athletic | – | Chasetown | | 4:0 (1:0) * |
| Oldham |
FA Cup 2004/05, Preliminary Round |
| | | Belper Town | – | Chasetown | | 2:0 * |
| |
FA Cup 2003/04, Preliminary Round |
| | | Chasetown | – | Sutton Coldfield Town | | 1:2 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Chasetown | – | Spalding United | | 0:1 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Halesowen Town | – | Chasetown | | 2:0 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Chasetown | – | Alfreton Town | | 0:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Matlock Town | – | Chasetown | | 1:0 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Chasetown | – | Buxton | | 0:1 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Valley Sports Rugby | – | Chasetown | | 1:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Gresley Rovers | – | Chasetown | | 2:1 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Chasetown | – | Solihull Borough | | 1:3 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Desborough Town | – | Chasetown | | 1:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Chasetown | – | Solihull Borough | | 0:1 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Chasetown | – | Braintree Town | | 0:2 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Valley Sports Rugby | – | Chasetown | | 3:0 * |
| |
FA Cup 1990/91, Preliminary Round |
| | | Chasetown | – | Evesham United | | 0:2 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Spalding United | – | Chasetown | | 3:0 * |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Chasetown | – | Tamworth | | 0:1 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Chasetown | – | Evesham United | | 0:2 |
| |
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