| 1 | Sat 13 Jul 2019 | 71-2 v DartfordGrays Athletic 1-2 Dartford | Friendly |
| 2 | Wed 31 Jul 2019 | 85-3 v KingstonianGrays Athletic 5-3 Kingstonian | Friendly |
| 3 | Sat 3 Aug 2019 | 101-2 v Dulwich HamletTonbridge Angels 1-2 Dulwich Hamlet | Vanarama National League South |
| 4 | Sat 3 Aug 2019 | 82-3 v Metropolitan PoliceMetropolitan Police 3-2 Grays Athletic | Friendly |
| 5 | Sat 10 Aug 2019 | 101-3 v Dorking WanderersDorking Wanderers 3-1 Tonbridge Angels | Vanarama National League South |
| 6 | Sat 10 Aug 2019 | 143-2 v VCD AthleticVCD Athletic 2-3 Grays Athletic | Friendly |
| 7 | Tue 13 Aug 2019 | 101-0 v Concord RangersTonbridge Angels 1-0 Concord Rangers | Vanarama National League South |
| 8 | Sat 17 Aug 2019 | 100-0 v Bath CityBath City 0-0 Tonbridge Angels | Vanarama National League South |
| 9 | Sat 24 Aug 2019 | 101-3 v Havant & WaterloovilleTonbridge Angels 1-3 Havant & Waterlooville | Vanarama National League South |
| 10 | Sat 24 Aug 2019 | 155-2 v Heybridge SwiftsGrays Athletic 5-2 Heybridge Swifts | Emirates FA Cup Preliminary Round |
| 11 | Mon 26 Aug 2019 | 102-4 v Welling UnitedWelling United 4-2 Tonbridge Angels | Vanarama National League South |
| 12 | Sat 31 Aug 2019 | 101-1 v WeymouthTonbridge Angels 1-1 Weymouth | Vanarama National League South |
| 13 | Sat 12 Oct 2019 | 105-1 v Braintree TownTonbridge Angels 5-1 Braintree Town | Vanarama National League South |
| 14 | Sat 12 Oct 2019 | 81-4 v LeatherheadMerstham 1-4 Leatherhead | BetVictor Isthmian Premier Division |
| 15 | Tue 15 Oct 2019 | 81-2 v Cray WanderersMerstham 1-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 16 | Sat 19 Oct 2019 | 101-2 v Chelmsford CityTonbridge Angels 1-2 Chelmsford City | Vanarama National League South |
| 17 | Sat 19 Oct 2019 | 4 0-4 v HorshamHorsham 4-0 Merstham | BetVictor Isthmian Premier Division |
| 18 | Tue 22 Oct 2019 | 81-2 v MargateMargate 2-1 Merstham | BetVictor Isthmian Premier Division |
| 19 | Sat 26 Oct 2019 | 141-3 v WealdstoneWealdstone 3-1 Tonbridge Angels | Vanarama National League South |
| 20 | Sat 26 Oct 2019 | 81-3 v Carshalton AthleticCarshalton Athletic 3-1 Merstham | Buildbase FA Trophy First Qualifying Round |
| 21 | Sat 2 Nov 2019 | 104-4 v Oxford CityTonbridge Angels 4-4 Oxford City | Vanarama National League South |
| 22 | Sat 16 Nov 2019 | 152-1 v St Albans CityTonbridge Angels 2-1 St Albans City | Vanarama National League South |
| 23 | Sat 23 Nov 2019 | 152-1 v Bognor Regis TownTonbridge Angels 2-1 Bognor Regis Town | Buildbase FA Trophy Third Qualifying Round |
| 24 | Tue 3 Dec 2019 | 80-1 v Hungerford TownHungerford Town 1-0 Tonbridge Angels | Vanarama National League South |
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