| 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 |
| 20 | 14/12/2019 | 44-0 v Staines TownStaines Town 0-4 Chertsey Town | BetVictor Isthmian South Central Division |
| 21 | 28/12/2019 | 43-3 v Bedfont SportsChertsey Town 3-3 Bedfont Sports | BetVictor Isthmian South Central Division |
| 22 | 4/1/2020 | 40-2 v WareWare 2-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 23 | 11/1/2020 | 43-0 v Harlow TownChertsey Town 3-0 Harlow Town | BetVictor Isthmian South Central Division |
| 24 | 18/1/2020 | 40-0 v Bracknell TownBracknell Town 0-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 25 | 25/1/2020 | 4 6-1 v Hertford TownChertsey Town 6-1 Hertford Town | BetVictor Isthmian South Central Division |
| 26 | 1/2/2020 | 44-1 v NorthwoodNorthwood 1-4 Chertsey Town | BetVictor Isthmian South Central Division |
| 27 | 4/2/2020 | 44-0 v Ashford Town (Middx)Chertsey Town 4-0 Ashford Town (Middx) | BetVictor Isthmian South Central Division |
| 28 | 8/2/2020 | 4 2-1 v Tooting & Mitcham UnitedTooting & Mitcham United 1-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 29 | 15/2/2020 | 46-3 v Staines TownChertsey Town 6-3 Staines Town | BetVictor Isthmian South Central Division |
| 30 | 22/2/2020 | 41-1 v FC RomaniaFC Romania 1-1 Chertsey Town | BetVictor Isthmian South Central Division |
| 31 | 7/3/2020 | 43-0 v WestfieldWestfield 0-3 Chertsey Town | BetVictor Isthmian South Central Division |
