| 1 | Sat 10 Aug 2019 | 21-1 v Bowers & PitseaBowers & Pitsea 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 2 | Tue 13 Aug 2019 | 21-1 v KingstonianWingate & Finchley 1-1 Kingstonian | BetVictor Isthmian Premier Division |
| 3 | Sat 17 Aug 2019 | 20-5 v Bognor Regis TownWingate & Finchley 0-5 Bognor Regis Town | BetVictor Isthmian Premier Division |
| 4 | Sat 24 Aug 2019 | 22-0 v Welwyn Garden CityWingate & Finchley 2-0 Welwyn Garden City | Emirates FA Cup Preliminary Round |
| 5 | Mon 26 Aug 2019 | 2 1-0 v Haringey BoroughWingate & Finchley 1-0 Haringey Borough | BetVictor Isthmian Premier Division |
| 6 | Sat 31 Aug 2019 | 20-2 v HornchurchHornchurch 2-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 7 | Sat 7 Sep 2019 | 24-1 v London ColneyWingate & Finchley 4-1 London Colney | Emirates FA Cup First Qualifying Round |
| 8 | Sat 14 Sep 2019 | 20-4 v MersthamWingate & Finchley 0-4 Merstham | BetVictor Isthmian Premier Division |
| 9 | Tue 17 Sep 2019 | 21-2 v HorshamHorsham 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 10 | Sat 28 Sep 2019 | 21-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 11 | Tue 1 Oct 2019 | 20-1 v CheshuntCheshunt 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 12 | Sat 12 Oct 2019 | 21-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 13 | Tue 15 Oct 2019 | 26-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 14 | Tue 22 Oct 2019 | 21-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 15 | Sat 26 Oct 2019 | 21-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 16 | Tue 29 Oct 2019 | 21-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 17 | Sat 2 Nov 2019 | 21-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 18 | Sat 9 Nov 2019 | 22-1 v LewesLewes 1-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 19 | Tue 12 Nov 2019 | 20-1 v Cray WanderersWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 20 | Sat 16 Nov 2019 | 22-3 v WorthingWingate & Finchley 2-3 Worthing | BetVictor Isthmian Premier Division |
| 21 | Tue 19 Nov 2019 | 23-2 v Dulwich HamletDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 22 | Sat 23 Nov 2019 | 22-0 v Bowers & PitseaWingate & Finchley 2-0 Bowers & Pitsea | Velocity Trophy |
| 23 | Tue 26 Nov 2019 | 23-1 v HendonHendon 1-3 Wingate & Finchley | Middlesex County Cup Second Round |
| 24 | Sat 30 Nov 2019 | 2 2-2 v Enfield TownEnfield Town 2-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 25 | Tue 3 Dec 2019 | 20-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 26 | Sat 7 Dec 2019 | 22-3 v HornchurchWingate & Finchley 2-3 Hornchurch | BetVictor Isthmian Premier Division |
| 27 | Sat 14 Dec 2019 | 23-3 v Corinthian-CasualsCorinthian-Casuals 3-3 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 28 | Sat 21 Dec 2019 | 21-2 v Potters Bar TownWingate & Finchley 1-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 29 | Wed 1 Jan 2020 | 21-2 v Haringey BoroughHaringey Borough 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 30 | Sat 4 Jan 2020 | 150-0 v Cray WanderersCray Wanderers 0-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 31 | Tue 7 Jan 2020 | 71-2 v LeatherheadWingate & Finchley 1-2 Leatherhead | BetVictor Isthmian Premier Division |
| 32 | Sat 11 Jan 2020 | 71-2 v CheshuntWingate & Finchley 1-2 Cheshunt | BetVictor Isthmian Premier Division |
| 33 | Sat 18 Jan 2020 | 162-3 v Carshalton AthleticCarshalton Athletic 3-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 34 | Tue 21 Jan 2020 | 71-3 v MargateWingate & Finchley 1-3 Margate | Velocity Trophy |
| 35 | Tue 28 Jan 2020 | 20-1 v BrentfordWingate & Finchley 0-1 Brentford | Middlesex County Cup Quarter Final |
| 36 | Sat 1 Feb 2020 | 171-0 v Bishop's StortfordBishop's Stortford 0-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 37 | Tue 11 Feb 2020 | 21-0 v Corinthian-CasualsWingate & Finchley 1-0 Corinthian-Casuals | London County Cup Quarter Final |
| 38 | Sat 15 Feb 2020 | 162-2 v Bowers & PitseaWingate & Finchley 2-2 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 39 | Sat 22 Feb 2020 | 71-0 v Folkestone InvictaFolkestone Invicta 0-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 40 | Sat 29 Feb 2020 | 71-1 v LewesWingate & Finchley 1-1 Lewes | BetVictor Isthmian Premier Division |
| 41 | Tue 10 Mar 2020 | 70-1 v MargateMargate 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
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