| 1 | Sat 10 Aug 2019 | 151-1 v Bowers & PitseaBowers & Pitsea 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 2 | Tue 13 Aug 2019 | 151-1 v KingstonianWingate & Finchley 1-1 Kingstonian | BetVictor Isthmian Premier Division |
| 3 | Sat 24 Aug 2019 | 32-0 v Welwyn Garden CityWingate & Finchley 2-0 Welwyn Garden City | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 31-0 v Haringey BoroughWingate & Finchley 1-0 Haringey Borough | BetVictor Isthmian Premier Division |
| 5 | Sat 31 Aug 2019 | 30-2 v HornchurchHornchurch 2-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 6 | Sat 7 Sep 2019 | 34-1 v London ColneyWingate & Finchley 4-1 London Colney | Emirates FA Cup First Qualifying Round |
| 7 | Tue 17 Sep 2019 | 3 1-2 v HorshamHorsham 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 8 | Sat 21 Sep 2019 | 32-4 v Maldon & TiptreeMaldon & Tiptree 4-2 Wingate & Finchley | Emirates FA Cup Second Qualifying Round |
| 9 | Sat 28 Sep 2019 | 31-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 10 | Tue 1 Oct 2019 | 30-1 v CheshuntCheshunt 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 11 | Sat 12 Oct 2019 | 31-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 12 | Tue 15 Oct 2019 | 36-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 13 | Tue 22 Oct 2019 | 31-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 14 | Sat 26 Oct 2019 | 31-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 15 | Tue 29 Oct 2019 | 31-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 16 | Sat 2 Nov 2019 | 3 1-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 17 | Sat 16 Nov 2019 | 162-3 v WorthingWingate & Finchley 2-3 Worthing | BetVictor Isthmian Premier Division |
| 18 | Tue 19 Nov 2019 | 33-2 v Dulwich HamletDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 19 | Sat 23 Nov 2019 | 32-0 v Bowers & PitseaWingate & Finchley 2-0 Bowers & Pitsea | Velocity Trophy |
| 20 | Tue 26 Nov 2019 | 153-1 v HendonHendon 1-3 Wingate & Finchley | Middlesex County Cup Second Round |
| 21 | Tue 3 Dec 2019 | 150-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 22 | Sat 7 Dec 2019 | 152-3 v HornchurchWingate & Finchley 2-3 Hornchurch | BetVictor Isthmian Premier Division |
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