| 1 | 10/8/2019 | 2-0 v Salford CityCrawley Town 2-0 Salford City | Sky Bet League Two |
| 2 | 13/8/2019 | 3-2 v WalsallWalsall 2-3 Crawley Town | Carabao Cup First Round |
| 3 | 17/8/2019 | 2-2 v Scunthorpe UnitedScunthorpe United 2-2 Crawley Town | Sky Bet League Two |
| 4 | 20/8/2019 | 1-2 v Crewe AlexandraCrawley Town 1-2 Crewe Alexandra | Sky Bet League Two |
| 5 | 24/8/2019 | 3-2 v Leyton OrientLeyton Orient 2-3 Crawley Town | Sky Bet League Two |
| 6 | 27/8/2019 | 1-0 v Norwich CityCrawley Town 1-0 Norwich City | Carabao Cup Second Round |
| 7 | 31/8/2019 | 1-0 v Cheltenham TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 8 | 7/9/2019 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Crawley Town | Sky Bet League Two |
| 9 | 21/9/2019 | 2-2 v Northampton TownNorthampton Town 2-2 Crawley Town | Sky Bet League Two |
| 10 | 24/9/2019 | 1-1 v Stoke CityCrawley Town 1-1 Stoke City | Carabao Cup Third Round |
| 11 | 28/9/2019 | 2-3 v WalsallCrawley Town 2-3 Walsall | Sky Bet League Two |
| 12 | 5/10/2019 | 1-3 v Forest Green RoversForest Green Rovers 3-1 Crawley Town | Sky Bet League Two |
| 13 | 12/10/2019 | 2-1 v Colchester UnitedCrawley Town 2-1 Colchester United | Sky Bet League Two |
| 14 | 19/10/2019 | 1-2 v Bradford CityBradford City 2-1 Crawley Town | Sky Bet League Two |
| 15 | 22/10/2019 | 1-1 v Newport CountyNewport County 1-1 Crawley Town | Sky Bet League Two |
| 16 | 29/10/2019 | 1-3 v Colchester UnitedCrawley Town 1-3 Colchester United | Carabao Cup Fourth Round |
| 17 | 2/11/2019 | 1-2 v Cambridge UnitedCambridge United 2-1 Crawley Town | Sky Bet League Two |
| 18 | 9/11/2019 | 4-1 v Scunthorpe UnitedCrawley Town 4-1 Scunthorpe United | Emirates FA Cup First Round |
| 19 | 12/11/2019 | 1-4 v Oxford UnitedCrawley Town 1-4 Oxford United | Checkatrade Trophy Southern Group B |
| 20 | 23/11/2019 | 0-1 v Exeter CityCrawley Town 0-1 Exeter City | Sky Bet League Two |
| 21 | 1/12/2019 | 1-2 v Fleetwood TownCrawley Town 1-2 Fleetwood Town | Emirates FA Cup Second Round |
