| 1 | Sat 14 Sep 2019 | 120-4 v MersthamWingate & Finchley 0-4 Merstham | BetVictor Isthmian Premier Division |
| 2 | Sat 28 Sep 2019 | 5 1-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 3 | Tue 1 Oct 2019 | 5 0-1 v CheshuntCheshunt 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 4 | Sat 12 Oct 2019 | 51-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 5 | Tue 15 Oct 2019 | 56-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 6 | Tue 22 Oct 2019 | 51-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 7 | Sat 26 Oct 2019 | 51-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 8 | Tue 29 Oct 2019 | 51-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 9 | Sat 2 Nov 2019 | 51-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 10 | Sat 9 Nov 2019 | 5 2-1 v LewesLewes 1-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 11 | Tue 12 Nov 2019 | 50-1 v Cray WanderersWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 12 | Sat 16 Nov 2019 | 5 2-3 v WorthingWingate & Finchley 2-3 Worthing | BetVictor Isthmian Premier Division |
| 13 | Tue 26 Nov 2019 | 53-1 v HendonHendon 1-3 Wingate & Finchley | Middlesex County Cup Second Round |
| 14 | Sat 30 Nov 2019 | 52-2 v Enfield TownEnfield Town 2-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 15 | Tue 3 Dec 2019 | 50-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 16 | Sat 7 Dec 2019 | 52-3 v HornchurchWingate & Finchley 2-3 Hornchurch | BetVictor Isthmian Premier Division |
| 17 | Sat 14 Dec 2019 | 53-3 v Corinthian-CasualsCorinthian-Casuals 3-3 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 18 | Sat 21 Dec 2019 | 51-2 v Potters Bar TownWingate & Finchley 1-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 19 | Wed 1 Jan 2020 | 51-2 v Haringey BoroughHaringey Borough 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 20 | Sat 18 Jan 2020 | 52-3 v Carshalton AthleticCarshalton Athletic 3-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
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