| 1 | 3/8/2019 | 1-0 v Southend UnitedCoventry City 1-0 Southend United | Sky Bet League One |
| 2 | 10/8/2019 | 0-0 v Bolton WanderersBolton Wanderers 0-0 Coventry City | Sky Bet League One |
| 3 | 13/8/2019 | 4-1 v Exeter CityCoventry City 4-1 Exeter City | Carabao Cup First Round |
| 4 | 17/8/2019 | 2-0 v Bristol RoversCoventry City 2-0 Bristol Rovers | Sky Bet League One |
| 5 | 20/8/2019 | 3-3 v PortsmouthPortsmouth 3-3 Coventry City | Sky Bet League One |
| 6 | 27/8/2019 | 0-3 v WatfordWatford 3-0 Coventry City | Carabao Cup Second Round |
| 7 | 31/8/2019 | 3-3 v Oxford UnitedOxford United 3-3 Coventry City | Sky Bet League One |
| 8 | 7/9/2019 | 3-2 v BlackpoolCoventry City 3-2 Blackpool | Sky Bet League One |
| 9 | 14/9/2019 | 0-0 v Burton AlbionBurton Albion 0-0 Coventry City | Sky Bet League One |
| 10 | 17/9/2019 | 2-1 v AFC WimbledonCoventry City 2-1 AFC Wimbledon | Sky Bet League One |
| 11 | 28/9/2019 | 1-1 v Doncaster RoversCoventry City 1-1 Doncaster Rovers | Sky Bet League One |
| 12 | 5/10/2019 | 0-4 v Rotherham UnitedRotherham United 4-0 Coventry City | Sky Bet League One |
| 13 | 13/10/2019 | 0-1 v Tranmere RoversCoventry City 0-1 Tranmere Rovers | Sky Bet League One |
| 14 | 19/10/2019 | 0-0 v Milton Keynes DonsMilton Keynes Dons 0-0 Coventry City | Sky Bet League One |
| 15 | 23/10/2019 | 2-1 v Fleetwood TownCoventry City 2-1 Fleetwood Town | Sky Bet League One |
| 16 | 26/10/2019 | 2-2 v Peterborough UnitedPeterborough United 2-2 Coventry City | Sky Bet League One |
| 17 | 9/11/2019 | 2-0 v Colchester UnitedColchester United 0-2 Coventry City | Emirates FA Cup First Round |
| 18 | 16/11/2019 | 2-1 v RochdaleCoventry City 2-1 Rochdale | Sky Bet League One |
| 19 | 23/11/2019 | 1-1 v SunderlandSunderland 1-1 Coventry City | Sky Bet League One |
| 20 | 1/12/2019 | 1-1 v Ipswich TownCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 21 | 7/12/2019 | 1-1 v Ipswich TownCoventry City 1-1 Ipswich Town | Sky Bet League One |
| 22 | 10/12/2019 | 2-1 v Ipswich TownIpswich Town 1-2 Coventry City | Emirates FA Cup Second Round Replay |
| 23 | 14/12/2019 | 1-2 v Shrewsbury TownShrewsbury Town 2-1 Coventry City | Sky Bet League One |
| 24 | 21/12/2019 | 1-0 v Lincoln CityCoventry City 1-0 Lincoln City | Sky Bet League One |
| 25 | 29/12/2019 | 4-1 v Wycombe WanderersWycombe Wanderers 1-4 Coventry City | Sky Bet League One |
| 26 | 1/1/2020 | 4-1 v Tranmere RoversTranmere Rovers 1-4 Coventry City | Sky Bet League One |
| 27 | 5/1/2020 | 2-2 v Bristol RoversBristol Rovers 2-2 Coventry City | Emirates FA Cup Third Round |
| 28 | 11/1/2020 | 1-1 v Milton Keynes DonsCoventry City 1-1 Milton Keynes Dons | Sky Bet League One |
| 29 | 18/1/2020 | 1-0 v Doncaster RoversDoncaster Rovers 0-1 Coventry City | Sky Bet League One |
| 30 | 25/1/2020 | 0-0 v Birmingham CityCoventry City 0-0 Birmingham City | Emirates FA Cup Fourth Round |
| 31 | 28/1/2020 | 0-0 v Fleetwood TownFleetwood Town 0-0 Coventry City | Sky Bet League One |
| 32 | 1/2/2020 | 2-1 v Bristol RoversBristol Rovers 1-2 Coventry City | Sky Bet League One |
| 33 | 4/2/2020 | 2-2 v Birmingham CityBirmingham City 2-2 Coventry City | Emirates FA Cup Fourth Round Replay |
| 34 | 8/2/2020 | 2-1 v Bolton WanderersCoventry City 2-1 Bolton Wanderers | Sky Bet League One |
| 35 | 11/2/2020 | 1-0 v PortsmouthCoventry City 1-0 Portsmouth | Sky Bet League One |
| 36 | 15/2/2020 | 2-0 v Southend UnitedSouthend United 0-2 Coventry City | Sky Bet League One |
| 37 | 22/2/2020 | 2-1 v RochdaleRochdale 1-2 Coventry City | Sky Bet League One |
