| 1 | 20/8/2019 | 43-0 v South ParkChertsey Town 3-0 South Park | BetVictor Isthmian South Central Division |
| 2 | 24/8/2019 | 45-1 v Erith & BelvedereChertsey Town 5-1 Erith & Belvedere | Emirates FA Cup Preliminary Round |
| 3 | 26/8/2019 | 40-1 v Bedfont SportsBedfont Sports 1-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 4 | 31/8/2019 | 4 1-1 v WareChertsey Town 1-1 Ware | BetVictor Isthmian South Central Division |
| 5 | 7/9/2019 | 4 4-1 v Sheppey UnitedChertsey Town 4-1 Sheppey United | Emirates FA Cup First Qualifying Round |
| 6 | 14/9/2019 | 4 4-2 v MarlowMarlow 2-4 Chertsey Town | BetVictor Isthmian South Central Division |
| 7 | 17/9/2019 | 42-1 v Ashford Town (Middx)Ashford Town (Middx) 1-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 8 | 22/9/2019 | 43-1 v BiggleswadeBiggleswade 1-3 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 9 | 5/10/2019 | 41-6 v Maldon & TiptreeMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 10 | 8/10/2019 | 148-2 v NorthwoodChertsey Town 8-2 Northwood | BetVictor Isthmian South Central Division |
| 11 | 12/10/2019 | 170-1 v MarlowMarlow 1-0 Chertsey Town | Buildbase FA Trophy Preliminary Round |
| 12 | 19/10/2019 | 42-1 v Bracknell TownChertsey Town 2-1 Bracknell Town | BetVictor Isthmian South Central Division |
| 13 | 26/10/2019 | 162-2 v South ParkChertsey Town 2-2 South Park | Velocity Trophy Group 10 |
| 14 | 29/10/2019 | 16 3-2 v Hertford TownHertford Town 2-3 Chertsey Town | BetVictor Isthmian South Central Division |
| 15 | 2/11/2019 | 187-0 v FC RomaniaChertsey Town 7-0 FC Romania | BetVictor Isthmian South Central Division |
| 16 | 5/11/2019 | 173-1 v Tooting & Mitcham UnitedTooting & Mitcham United 1-3 Chertsey Town | Velocity Trophy Group 10 |
| 17 | 12/11/2019 | 152-4 v BarkingBarking 4-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 18 | 16/11/2019 | 4 2-2 v WestfieldChertsey Town 2-2 Westfield | BetVictor Isthmian South Central Division |
| 19 | 19/11/2019 | 151-0 v WhyteleafeWhyteleafe 0-1 Chertsey Town | Velocity Trophy Group 10 |
