| 1 | Tue 4 Dec 2018 | 6 3-3 v Bowers & PitseaBowers & Pitsea 3-3 Wingate & Finchley | Velocity Trophy Second Round |
| 2 | Tue 11 Dec 2018 | 15 0-2 v Harlow TownWingate & Finchley 0-2 Harlow Town | Bostik League Premier Division |
| 3 | Sat 15 Dec 2018 | 62-0 v Dulwich HamletWingate & Finchley 2-0 Dulwich Hamlet | Buildbase FA Trophy First Round |
| 4 | Sat 22 Dec 2018 | 62-0 v Carshalton AthleticWingate & Finchley 2-0 Carshalton Athletic | Bostik League Premier Division |
| 5 | Wed 26 Dec 2018 | 7 1-4 v Enfield TownEnfield Town 4-1 Wingate & Finchley | Bostik League Premier Division |
| 6 | Tue 1 Jan 2019 | 60-4 v Haringey BoroughWingate & Finchley 0-4 Haringey Borough | Bostik League Premier Division |
| 7 | Sat 5 Jan 2019 | 80-3 v MersthamMerstham 3-0 Wingate & Finchley | Bostik League Premier Division |
| 8 | Sat 12 Jan 2019 | 4 2-4 v Hemel Hempstead TownHemel Hempstead Town 4-2 Wingate & Finchley | Buildbase FA Trophy Second Round |
| 9 | Tue 15 Jan 2019 | 62-3 v BrentfordWingate & Finchley 2-3 Brentford | London County Cup Quarter Final |
| 10 | Sat 19 Jan 2019 | 62-4 v LewesLewes 4-2 Wingate & Finchley | Bostik League Premier Division |
| 11 | Sat 26 Jan 2019 | 6 2-2 v Brightlingsea RegentWingate & Finchley 2-2 Brightlingsea Regent | Bostik League Premier Division |
| 12 | Sat 2 Feb 2019 | 61-2 v LeatherheadLeatherhead 2-1 Wingate & Finchley | Bostik League Premier Division |
| 13 | Sat 9 Feb 2019 | 61-1 v WhitehawkWingate & Finchley 1-1 Whitehawk | Bostik League Premier Division |
| 14 | Wed 13 Feb 2019 | 61-2 v Tonbridge AngelsWingate & Finchley 1-2 Tonbridge Angels | Bostik League Premier Division |
| 15 | Sat 16 Feb 2019 | 4 2-2 v Folkestone InvictaFolkestone Invicta 2-2 Wingate & Finchley | Bostik League Premier Division |
| 16 | Tue 19 Feb 2019 | 6 2-2 v Bishop's StortfordWingate & Finchley 2-2 Bishop's Stortford | Bostik League Premier Division |
| 17 | Sat 16 Mar 2019 | 6 7-2 v Harlow TownHarlow Town 2-7 Wingate & Finchley | Bostik League Premier Division |
| 18 | Sat 23 Mar 2019 | 6 4-2 v Potters Bar TownWingate & Finchley 4-2 Potters Bar Town | Bostik League Premier Division |
| 19 | Sat 20 Apr 2019 | 40-1 v MargateWingate & Finchley 0-1 Margate | Bostik League Premier Division |
| 20 | Mon 22 Apr 2019 | 8 2-1 v Haringey BoroughHaringey Borough 1-2 Wingate & Finchley | Bostik League Premier Division |
| 21 | Sat 27 Apr 2019 | 84-2 v Burgess Hill TownWingate & Finchley 4-2 Burgess Hill Town | Bostik League Premier Division |
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