FA Cup 2023/24, Extra Preliminary Round |
 | 08.08.2023 | | Walsall Wood | – | Highgate United | | 2:1 (1:1) * |
| Walsall Wood |
FA Cup 2022/23, First Qualifying Round |
| 06.09.2022 | | Highgate United | – | Barwell | | 0:3 (0:1) * |
| Solihull |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Highgate United | – | Coleshill Town | | 1:4 (0:2) |
| Solihull |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Highgate United | – | AFC Bridgnorth | | 0:3 |
| Solihull |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Lichfield City | – | Highgate United | | 3:2 (2:1) |
| Lichfield |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Highgate United | – | Stourbridge | | 1:2 (0:1) |
| Solihull |
FA Cup 2017/18, Extra Preliminary Round |
| 08.08.2017 | | Highgate United | – | Tividale | | 2:3 * |
| Solihull |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Westfields | – | Highgate United | | 4:2 |
| Hereford |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Tipton Town | – | Highgate United | | 4:1 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Bridgnorth Town | – | Highgate United | | 4:0 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 18.08.2009 | | Malvern Town | – | Highgate United | | 2:1 * |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Highgate United | – | Romulus | | 1:4 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Stourbridge | – | Highgate United | | 2:1 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Gresley Rovers | – | Highgate United | | 4:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Highgate United | – | Chasetown | | 0:3 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Stratford Town | – | Highgate United | | 3:1 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Hinckley Athletic | – | Highgate United | | 2:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Highgate United | – | Rushden Town | | 0:4 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Bilston Town | – | Highgate United | | 2:0 * |
| |
FA Cup 1986/87, Preliminary Round |
| | | Highgate United | – | Banbury United | | 1:3 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Oldswinford | – | Highgate United | | 2:1 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Highgate United | – | Mangotsfield United | | 1:3 * |
| |
FA Cup 1983/84, Preliminary Round |
| | | Highgate United | – | Bridgnorth Town | | 1:2 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Valley Sports Rugby | – | Highgate United | | 3:1 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Malvern Town | – | Highgate United | | 2:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Witton Albion | – | Highgate United | | 3:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Highgate United | – | Brereton Social | | 0:2 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Worcester City | – | Highgate United | | 3:2 * |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Highgate United | – | Kidderminster Harriers | | 0:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Darlaston | – | Highgate United | | 2:1 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Gornal Athletic | – | Highgate United | | 1:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Kidderminster Harriers | – | Highgate United | | 5:2 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Telford United | – | Highgate United | | 2:0 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Bromsgrove Rovers | – | Highgate United | | 2:1 |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Redditch United | – | Highgate United | | 3:0 |
| |
FA Cup 1970/71, Preliminary Round |
| | | Highgate United | – | Worcester City | | 0:5 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Dudley Town | – | Highgate United | | 3:0 |
| |
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