FA Cup 2022/23, Extra Preliminary Round |
| 09.08.2022 | | Windsor | | Royal Wootton Bassett Town | | 0:2 (0:1) * |
| Windsor |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Royal Wootton Bassett Town | | Windsor | | 1:1 (0:0) |
| Wootton Bassett |
FA Cup 2021/22, Extra Preliminary Round |
| 08.08.2021 | | Tuffley Rovers | | Windsor | | 3:2 |
| Windsor |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Wantage Town | | Windsor | | 3:2 |
| Wantage |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Aylesbury Vale Dynamos | | Windsor | | 1:2 |
| Aylesbury |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Windsor | | Reading City | | 0:3 (0:0) |
| Windsor |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Cirencester Town | | Windsor | | 5:0 (2:0) |
| Cirencester |
FA Cup 2018/19, Extra Preliminary Round |
| 15.08.2018 | | Highworth Town | | Windsor | | 1:2 (0:2) * |
| Highworth |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Windsor | | Highworth Town | | 3:3 (1:1) |
| Windsor |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Windsor | | Wembley | | 1:4 (0:1) |
| Windsor |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Bedfont Sports | | Windsor | | 3:2 |
| London |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Windsor | | AFC Dunstable | | 0:1 |
| Windsor |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Windsor | | Godalming Town | | 0:2 |
| Windsor |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Brimscombe & Thrupp | | Windsor | | 1:2 |
| Brimscombe & Thrupp |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Windsor | | Highmoor Ibis | | 1:3 |
| Windsor |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Newbury | | Windsor | | 1:4 |
| Newbury |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Windsor | | Didcot Town | | 0:1 (0:0) |
| Windsor |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Aylesbury | | Windsor | | 0:2 |
| Aylesbury |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Flackwell Heath | | Windsor | | 0:1 |
| |