| 1 | Sat 5 Sep 2020 | 43-2 v Boreham WoodWingate & Finchley 3-2 Boreham Wood | Friendly |
| 2 | Sun 20 Sep 2020 | 4 1-2 v Bowers & PitseaWingate & Finchley 1-2 Bowers & Pitsea | Isthmian League - Premier Division |
| 3 | Wed 23 Sep 2020 | 41-4 v Folkestone InvictaWingate & Finchley 1-4 Folkestone Invicta | Emirates FA Cup First Qualifying Round |
| 4 | Sat 26 Sep 2020 | 41-4 v Folkestone InvictaFolkestone Invicta 4-1 Wingate & Finchley | Isthmian League - Premier Division |
| 5 | Wed 30 Sep 2020 | 4 2-3 v KingstonianKingstonian 3-2 Wingate & Finchley | Isthmian League - Premier Division |
| 6 | Sat 3 Oct 2020 | 4 4-1 v LewesWingate & Finchley 4-1 Lewes | Isthmian League - Premier Division |
| 7 | Tue 6 Oct 2020 | 43-2 v HornchurchHornchurch 2-3 Wingate & Finchley | Isthmian League - Premier Division |
| 8 | Sat 10 Oct 2020 | 41-2 v HorshamWingate & Finchley 1-2 Horsham | Isthmian League - Premier Division |
| 9 | Tue 20 Oct 2020 | 44-1 v Corinthian-CasualsWingate & Finchley 4-1 Corinthian-Casuals | Isthmian League - Premier Division |
| 10 | Tue 3 Nov 2020 | 42-2 v CheshuntWingate & Finchley 2-2 Cheshunt | Isthmian League - Premier Division |
| 11 | Tue 8 Dec 2020 | 41-4 v HornchurchHornchurch 4-1 Wingate & Finchley | Buildbase FA Trophy First Round |
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