| 1 | 10/8/2019 | 31-1 v CobhamChertsey Town 1-1 Cobham | Emirates FA Cup Extra Preliminary Round |
| 2 | 17/8/2019 | 32-2 v UxbridgeUxbridge 2-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 3 | 20/8/2019 | 33-0 v South ParkChertsey Town 3-0 South Park | BetVictor Isthmian South Central Division |
| 4 | 24/8/2019 | 35-1 v Erith & BelvedereChertsey Town 5-1 Erith & Belvedere | Emirates FA Cup Preliminary Round |
| 5 | 26/8/2019 | 30-1 v Bedfont SportsBedfont Sports 1-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 6 | 31/8/2019 | 31-1 v WareChertsey Town 1-1 Ware | BetVictor Isthmian South Central Division |
| 7 | 7/9/2019 | 34-1 v Sheppey UnitedChertsey Town 4-1 Sheppey United | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 34-2 v MarlowMarlow 2-4 Chertsey Town | BetVictor Isthmian South Central Division |
| 9 | 17/9/2019 | 32-1 v Ashford Town (Middx)Ashford Town (Middx) 1-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 10 | 22/9/2019 | 33-1 v BiggleswadeBiggleswade 1-3 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 11 | 28/9/2019 | 33-1 v Faversham TownFaversham Town 1-3 Chertsey Town | Buildbase FA Trophy Extra Preliminary Round |
| 12 | 5/10/2019 | 31-6 v Maldon & TiptreeMaldon & Tiptree 6-1 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 13 | 8/10/2019 | 38-2 v NorthwoodChertsey Town 8-2 Northwood | BetVictor Isthmian South Central Division |
| 14 | 12/10/2019 | 30-1 v MarlowMarlow 1-0 Chertsey Town | Buildbase FA Trophy Preliminary Round |
| 15 | 19/10/2019 | 32-1 v Bracknell TownChertsey Town 2-1 Bracknell Town | BetVictor Isthmian South Central Division |
| 16 | 26/10/2019 | 32-2 v South ParkChertsey Town 2-2 South Park | Velocity Trophy Group 10 |
| 17 | 29/10/2019 | 33-2 v Hertford TownHertford Town 2-3 Chertsey Town | BetVictor Isthmian South Central Division |
| 18 | 2/11/2019 | 37-0 v FC RomaniaChertsey Town 7-0 FC Romania | BetVictor Isthmian South Central Division |
| 19 | 9/11/2019 | 31-2 v Chalfont St PeterChalfont St Peter 2-1 Chertsey Town | BetVictor Isthmian South Central Division |
| 20 | 12/11/2019 | 32-4 v BarkingBarking 4-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 21 | 16/11/2019 | 32-2 v WestfieldChertsey Town 2-2 Westfield | BetVictor Isthmian South Central Division |
| 22 | 19/11/2019 | 31-0 v WhyteleafeWhyteleafe 0-1 Chertsey Town | Velocity Trophy Group 10 |
| 23 | 23/11/2019 | 3 0-2 v Waltham AbbeyWaltham Abbey 2-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 24 | 30/11/2019 | 31-1 v Hanwell TownChertsey Town 1-1 Hanwell Town | BetVictor Isthmian South Central Division |
| 25 | 7/12/2019 | 30-5 v Tooting & Mitcham UnitedChertsey Town 0-5 Tooting & Mitcham United | BetVictor Isthmian South Central Division |
