| 1 | 10/8/2019 | 21-1 v CobhamChertsey Town 1-1 Cobham | Emirates FA Cup Extra Preliminary Round |
| 2 | 17/8/2019 | 22-2 v UxbridgeUxbridge 2-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 3 | 20/8/2019 | 23-0 v South ParkChertsey Town 3-0 South Park | BetVictor Isthmian South Central Division |
| 4 | 31/8/2019 | 21-1 v WareChertsey Town 1-1 Ware | BetVictor Isthmian South Central Division |
| 5 | 7/9/2019 | 24-1 v Sheppey UnitedChertsey Town 4-1 Sheppey United | Emirates FA Cup First Qualifying Round |
| 6 | 14/9/2019 | 24-2 v MarlowMarlow 2-4 Chertsey Town | BetVictor Isthmian South Central Division |
| 7 | 17/9/2019 | 22-1 v Ashford Town (Middx)Ashford Town (Middx) 1-2 Chertsey Town | BetVictor Isthmian South Central Division |
| 8 | 22/9/2019 | 23-1 v BiggleswadeBiggleswade 1-3 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 9 | 28/9/2019 | 143-1 v Faversham TownFaversham Town 1-3 Chertsey Town | Buildbase FA Trophy Extra Preliminary Round |
| 10 | 8/10/2019 | 28-2 v NorthwoodChertsey Town 8-2 Northwood | BetVictor Isthmian South Central Division |
| 11 | 12/10/2019 | 2 0-1 v MarlowMarlow 1-0 Chertsey Town | Buildbase FA Trophy Preliminary Round |
| 12 | 19/10/2019 | 22-1 v Bracknell TownChertsey Town 2-1 Bracknell Town | BetVictor Isthmian South Central Division |
| 13 | 26/10/2019 | 152-2 v South ParkChertsey Town 2-2 South Park | Velocity Trophy Group 10 |
| 14 | 29/10/2019 | 23-2 v Hertford TownHertford Town 2-3 Chertsey Town | BetVictor Isthmian South Central Division |
| 15 | 2/11/2019 | 27-0 v FC RomaniaChertsey Town 7-0 FC Romania | BetVictor Isthmian South Central Division |
| 16 | 9/11/2019 | 21-2 v Chalfont St PeterChalfont St Peter 2-1 Chertsey Town | BetVictor Isthmian South Central Division |
| 17 | 23/11/2019 | 20-2 v Waltham AbbeyWaltham Abbey 2-0 Chertsey Town | BetVictor Isthmian South Central Division |
| 18 | 30/11/2019 | 21-1 v Hanwell TownChertsey Town 1-1 Hanwell Town | BetVictor Isthmian South Central Division |
| 19 | 7/12/2019 | 20-5 v Tooting & Mitcham UnitedChertsey Town 0-5 Tooting & Mitcham United | BetVictor Isthmian South Central Division |
