| 1 | Sat 28 Sep 2019 | 61-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 2 | Tue 1 Oct 2019 | 6 0-1 v CheshuntCheshunt 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 3 | Sat 12 Oct 2019 | 61-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 4 | Tue 15 Oct 2019 | 66-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 5 | Tue 22 Oct 2019 | 61-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 6 | Sat 26 Oct 2019 | 6 1-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 7 | Tue 29 Oct 2019 | 6 1-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 8 | Sat 2 Nov 2019 | 6 1-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 9 | Sat 9 Nov 2019 | 62-1 v LewesLewes 1-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 10 | Tue 12 Nov 2019 | 60-1 v Cray WanderersWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 11 | Sat 16 Nov 2019 | 62-3 v WorthingWingate & Finchley 2-3 Worthing | BetVictor Isthmian Premier Division |
| 12 | Sat 23 Nov 2019 | 62-0 v Bowers & PitseaWingate & Finchley 2-0 Bowers & Pitsea | Velocity Trophy |
| 13 | Sat 30 Nov 2019 | 142-2 v Enfield TownEnfield Town 2-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 14 | Tue 3 Dec 2019 | 60-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 15 | Sat 7 Dec 2019 | 62-3 v HornchurchWingate & Finchley 2-3 Hornchurch | BetVictor Isthmian Premier Division |
| 16 | Sat 14 Dec 2019 | 63-3 v Corinthian-CasualsCorinthian-Casuals 3-3 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 17 | Sat 21 Dec 2019 | 61-2 v Potters Bar TownWingate & Finchley 1-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 18 | Sat 4 Jan 2020 | 50-0 v Cray WanderersCray Wanderers 0-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 19 | Tue 7 Jan 2020 | 51-2 v LeatherheadWingate & Finchley 1-2 Leatherhead | BetVictor Isthmian Premier Division |
| 20 | Sat 11 Jan 2020 | 5 1-2 v CheshuntWingate & Finchley 1-2 Cheshunt | BetVictor Isthmian Premier Division |
| 21 | Sat 18 Jan 2020 | 62-3 v Carshalton AthleticCarshalton Athletic 3-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 22 | Tue 21 Jan 2020 | 61-3 v MargateWingate & Finchley 1-3 Margate | Velocity Trophy |
| 23 | Sat 25 Jan 2020 | 60-0 v Brightlingsea RegentWingate & Finchley 0-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 24 | Tue 28 Jan 2020 | 6 0-1 v BrentfordWingate & Finchley 0-1 Brentford | Middlesex County Cup Quarter Final |
| 25 | Sat 1 Feb 2020 | 61-0 v Bishop's StortfordBishop's Stortford 0-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 26 | Sat 8 Feb 2020 | 62-1 v East Thurrock UnitedWingate & Finchley 2-1 East Thurrock United | BetVictor Isthmian Premier Division |
| 27 | Tue 11 Feb 2020 | 61-0 v Corinthian-CasualsWingate & Finchley 1-0 Corinthian-Casuals | London County Cup Quarter Final |
| 28 | Sat 15 Feb 2020 | 6 2-2 v Bowers & PitseaWingate & Finchley 2-2 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 29 | Sat 29 Feb 2020 | 161-1 v LewesWingate & Finchley 1-1 Lewes | BetVictor Isthmian Premier Division |
| 30 | Sat 7 Mar 2020 | 62-4 v WorthingWorthing 4-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 31 | Tue 10 Mar 2020 | 60-1 v MargateMargate 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
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