| 1 | Wed 1 Jan 2020 | 31-2 v Haringey BoroughHaringey Borough 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 2 | Sat 4 Jan 2020 | 30-0 v Cray WanderersCray Wanderers 0-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 3 | Tue 7 Jan 2020 | 31-2 v LeatherheadWingate & Finchley 1-2 Leatherhead | BetVictor Isthmian Premier Division |
| 4 | Sat 11 Jan 2020 | 31-2 v CheshuntWingate & Finchley 1-2 Cheshunt | BetVictor Isthmian Premier Division |
| 5 | Sat 18 Jan 2020 | 32-3 v Carshalton AthleticCarshalton Athletic 3-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 6 | Tue 21 Jan 2020 | 31-3 v MargateWingate & Finchley 1-3 Margate | Velocity Trophy |
| 7 | Sat 25 Jan 2020 | 30-0 v Brightlingsea RegentWingate & Finchley 0-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 8 | Tue 28 Jan 2020 | 30-1 v BrentfordWingate & Finchley 0-1 Brentford | Middlesex County Cup Quarter Final |
| 9 | Sat 1 Feb 2020 | 31-0 v Bishop's StortfordBishop's Stortford 0-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 10 | Sat 8 Feb 2020 | 32-1 v East Thurrock UnitedWingate & Finchley 2-1 East Thurrock United | BetVictor Isthmian Premier Division |
| 11 | Sat 15 Feb 2020 | 3 2-2 v Bowers & PitseaWingate & Finchley 2-2 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 12 | Sat 22 Feb 2020 | 31-0 v Folkestone InvictaFolkestone Invicta 0-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 13 | Sat 29 Feb 2020 | 31-1 v LewesWingate & Finchley 1-1 Lewes | BetVictor Isthmian Premier Division |
| 14 | Sat 7 Mar 2020 | 32-4 v WorthingWorthing 4-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 15 | Tue 10 Mar 2020 | 30-1 v MargateMargate 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
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