| 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 | 24/8/2019 | 1-0 v GillinghamCoventry City 1-0 Gillingham | Sky Bet League One |
| 7 | 27/8/2019 | 0-3 v WatfordWatford 3-0 Coventry City | Carabao Cup Second Round |
| 8 | 31/8/2019 | 3-3 v Oxford UnitedOxford United 3-3 Coventry City | Sky Bet League One |
| 9 | 7/9/2019 | 3-2 v BlackpoolCoventry City 3-2 Blackpool | Sky Bet League One |
| 10 | 14/9/2019 | 0-0 v Burton AlbionBurton Albion 0-0 Coventry City | Sky Bet League One |
| 11 | 17/9/2019 | 2-1 v AFC WimbledonCoventry City 2-1 AFC Wimbledon | Sky Bet League One |
| 12 | 28/9/2019 | 1-1 v Doncaster RoversCoventry City 1-1 Doncaster Rovers | Sky Bet League One |
| 13 | 5/10/2019 | 0-4 v Rotherham UnitedRotherham United 4-0 Coventry City | Sky Bet League One |
| 14 | 13/10/2019 | 0-1 v Tranmere RoversCoventry City 0-1 Tranmere Rovers | Sky Bet League One |
| 15 | 19/10/2019 | 0-0 v Milton Keynes DonsMilton Keynes Dons 0-0 Coventry City | Sky Bet League One |
| 16 | 23/10/2019 | 2-1 v Fleetwood TownCoventry City 2-1 Fleetwood Town | Sky Bet League One |
| 17 | 26/10/2019 | 2-2 v Peterborough UnitedPeterborough United 2-2 Coventry City | Sky Bet League One |
| 18 | 2/11/2019 | 0-0 v Accrington StanleyCoventry City 0-0 Accrington Stanley | Sky Bet League One |
| 19 | 16/11/2019 | 2-1 v RochdaleCoventry City 2-1 Rochdale | Sky Bet League One |
| 20 | 23/11/2019 | 1-1 v SunderlandSunderland 1-1 Coventry City | Sky Bet League One |
| 21 | 1/12/2019 | 1-1 v Ipswich TownCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 22 | 3/12/2019 | 0-2 v Milton Keynes DonsMilton Keynes Dons 2-0 Coventry City | Checkatrade Trophy Second Round |
| 23 | 7/12/2019 | 1-1 v Ipswich TownCoventry City 1-1 Ipswich Town | Sky Bet League One |
