| 1 | Tue 13 Aug 2019 | 141-1 v KingstonianWingate & Finchley 1-1 Kingstonian | BetVictor Isthmian Premier Division |
| 2 | Sat 17 Aug 2019 | 140-5 v Bognor Regis TownWingate & Finchley 0-5 Bognor Regis Town | BetVictor Isthmian Premier Division |
| 3 | Sat 24 Aug 2019 | 42-0 v Welwyn Garden CityWingate & Finchley 2-0 Welwyn Garden City | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 71-0 v Haringey BoroughWingate & Finchley 1-0 Haringey Borough | BetVictor Isthmian Premier Division |
| 5 | Sat 31 Aug 2019 | 70-2 v HornchurchHornchurch 2-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 6 | Sat 7 Sep 2019 | 74-1 v London ColneyWingate & Finchley 4-1 London Colney | Emirates FA Cup First Qualifying Round |
| 7 | Sat 14 Sep 2019 | 140-4 v MersthamWingate & Finchley 0-4 Merstham | BetVictor Isthmian Premier Division |
| 8 | Tue 17 Sep 2019 | 71-2 v HorshamHorsham 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 9 | Sat 21 Sep 2019 | 72-4 v Maldon & TiptreeMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 10 | Sat 28 Sep 2019 | 151-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 11 | Tue 15 Oct 2019 | 86-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 12 | Tue 22 Oct 2019 | 81-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 13 | Sat 26 Oct 2019 | 81-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 14 | Tue 29 Oct 2019 | 101-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 15 | Sat 2 Nov 2019 | 151-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 16 | Sat 9 Nov 2019 | 112-1 v LewesLewes 1-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 17 | Tue 12 Nov 2019 | 11 0-1 v Cray WanderersWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 18 | Sat 16 Nov 2019 | 112-3 v WorthingWingate & Finchley 2-3 Worthing | BetVictor Isthmian Premier Division |
| 19 | Tue 19 Nov 2019 | 163-2 v Dulwich HamletDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 20 | Sat 23 Nov 2019 | 72-0 v Bowers & PitseaWingate & Finchley 2-0 Bowers & Pitsea | Velocity Trophy |
| 21 | Tue 26 Nov 2019 | 83-1 v HendonHendon 1-3 Wingate & Finchley | Middlesex County Cup Second Round |
| 22 | Tue 3 Dec 2019 | 160-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 23 | Sat 7 Dec 2019 | 72-3 v HornchurchWingate & Finchley 2-3 Hornchurch | BetVictor Isthmian Premier Division |
| 24 | Sat 14 Dec 2019 | 43-3 v Corinthian-CasualsCorinthian-Casuals 3-3 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 25 | Sat 21 Dec 2019 | 4 1-2 v Potters Bar TownWingate & Finchley 1-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 26 | Wed 1 Jan 2020 | 141-2 v Haringey BoroughHaringey Borough 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 27 | Sat 4 Jan 2020 | 80-0 v Cray WanderersCray Wanderers 0-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 28 | Tue 7 Jan 2020 | 81-2 v LeatherheadWingate & Finchley 1-2 Leatherhead | BetVictor Isthmian Premier Division |
| 29 | Sat 11 Jan 2020 | 171-2 v CheshuntWingate & Finchley 1-2 Cheshunt | BetVictor Isthmian Premier Division |
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