| 1 | Sat 24 Aug 2019 | 172-0 v Welwyn Garden CityWingate & Finchley 2-0 Welwyn Garden City | Emirates FA Cup Preliminary Round |
| 2 | Sat 7 Sep 2019 | 12 4-1 v London ColneyWingate & Finchley 4-1 London Colney | Emirates FA Cup First Qualifying Round |
| 3 | Sat 14 Sep 2019 | 160-4 v MersthamWingate & Finchley 0-4 Merstham | BetVictor Isthmian Premier Division |
| 4 | Tue 17 Sep 2019 | 171-2 v HorshamHorsham 2-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 5 | Sat 28 Sep 2019 | 91-1 v Folkestone InvictaWingate & Finchley 1-1 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 6 | Tue 1 Oct 2019 | 90-1 v CheshuntCheshunt 1-0 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 7 | Sat 12 Oct 2019 | 91-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 8 | Tue 15 Oct 2019 | 76-0 v Edgware TownWingate & Finchley 6-0 Edgware Town | Middlesex County Cup First Round |
| 9 | Tue 22 Oct 2019 | 71-2 v Bishop's StortfordWingate & Finchley 1-2 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 10 | Sat 26 Oct 2019 | 9 1-1 v Hayes & Yeading UnitedWingate & Finchley 1-1 Hayes & Yeading United | Buildbase FA Trophy First Qualifying Round |
| 11 | Tue 29 Oct 2019 | 91-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Wingate & Finchley | Buildbase FA Trophy First Qualifying Round |
| 12 | Sat 2 Nov 2019 | 141-3 v East Thurrock UnitedEast Thurrock United 3-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 13 | Tue 12 Nov 2019 | 16 0-1 v Cray WanderersWingate & Finchley 0-1 Cray Wanderers | BetVictor Isthmian Premier Division |
| 14 | Tue 19 Nov 2019 | 73-2 v Dulwich HamletDulwich Hamlet 2-3 Wingate & Finchley | London County Cup Second Round |
| 15 | Sat 23 Nov 2019 | 92-0 v Bowers & PitseaWingate & Finchley 2-0 Bowers & Pitsea | Velocity Trophy |
| 16 | Tue 26 Nov 2019 | 73-1 v HendonHendon 1-3 Wingate & Finchley | Middlesex County Cup Second Round |
| 17 | Sat 30 Nov 2019 | 7 2-2 v Enfield TownEnfield Town 2-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 18 | Tue 3 Dec 2019 | 70-2 v Carshalton AthleticWingate & Finchley 0-2 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 19 | Sat 14 Dec 2019 | 73-3 v Corinthian-CasualsCorinthian-Casuals 3-3 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 20 | Sat 21 Dec 2019 | 151-2 v Potters Bar TownWingate & Finchley 1-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 21 | Tue 21 Jan 2020 | 91-3 v MargateWingate & Finchley 1-3 Margate | Velocity Trophy |
| 22 | Tue 28 Jan 2020 | 140-1 v BrentfordWingate & Finchley 0-1 Brentford | Middlesex County Cup Quarter Final |
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