| 1 | Sat 10 Aug 2019 | 0-0 v Bolton WanderersBolton Wanderers 0-0 Coventry City | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 4-1 v Exeter CityCoventry City 4-1 Exeter City | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 2-0 v Bristol RoversCoventry City 2-0 Bristol Rovers | Sky Bet League One |
| 4 | Tue 20 Aug 2019 | 3-3 v PortsmouthPortsmouth 3-3 Coventry City | Sky Bet League One |
| 5 | Sat 24 Aug 2019 | 1-0 v GillinghamCoventry City 1-0 Gillingham | Sky Bet League One |
| 6 | Sat 31 Aug 2019 | 3-3 v Oxford UnitedOxford United 3-3 Coventry City | Sky Bet League One |
| 7 | Sat 7 Sep 2019 | 3-2 v BlackpoolCoventry City 3-2 Blackpool | Sky Bet League One |
| 8 | Sat 14 Sep 2019 | 0-0 v Burton AlbionBurton Albion 0-0 Coventry City | Sky Bet League One |
| 9 | Tue 17 Sep 2019 | 2-1 v AFC WimbledonCoventry City 2-1 AFC Wimbledon | Sky Bet League One |
| 10 | Sat 28 Sep 2019 | 1-1 v Doncaster RoversCoventry City 1-1 Doncaster Rovers | Sky Bet League One |
| 11 | Sat 5 Oct 2019 | 0-4 v Rotherham UnitedRotherham United 4-0 Coventry City | Sky Bet League One |
| 12 | Sun 13 Oct 2019 | 0-1 v Tranmere RoversCoventry City 0-1 Tranmere Rovers | Sky Bet League One |
| 13 | Sat 7 Dec 2019 | 1-1 v Ipswich TownCoventry City 1-1 Ipswich Town | Sky Bet League One |
| 14 | Tue 10 Dec 2019 | 2-1 v Ipswich TownIpswich Town 1-2 Coventry City | Emirates FA Cup Second Round Replay |
| 15 | Sat 14 Dec 2019 | 1-2 v Shrewsbury TownShrewsbury Town 2-1 Coventry City | Sky Bet League One |
| 16 | Sat 21 Dec 2019 | 1-0 v Lincoln CityCoventry City 1-0 Lincoln City | Sky Bet League One |
| 17 | Sun 29 Dec 2019 | 4-1 v Wycombe WanderersWycombe Wanderers 1-4 Coventry City | Sky Bet League One |
| 18 | Wed 1 Jan 2020 | 4-1 v Tranmere RoversTranmere Rovers 1-4 Coventry City | Sky Bet League One |
| 19 | Sun 5 Jan 2020 | 2-2 v Bristol RoversBristol Rovers 2-2 Coventry City | Emirates FA Cup Third Round |
| 20 | Sat 11 Jan 2020 | 1-1 v Milton Keynes DonsCoventry City 1-1 Milton Keynes Dons | Sky Bet League One |
| 21 | Sat 18 Jan 2020 | 1-0 v Doncaster RoversDoncaster Rovers 0-1 Coventry City | Sky Bet League One |
| 22 | Sat 25 Jan 2020 | 0-0 v Birmingham CityCoventry City 0-0 Birmingham City | Emirates FA Cup Fourth Round |
| 23 | Tue 28 Jan 2020 | 0-0 v Fleetwood TownFleetwood Town 0-0 Coventry City | Sky Bet League One |
| 24 | Sat 1 Feb 2020 | 2-1 v Bristol RoversBristol Rovers 1-2 Coventry City | Sky Bet League One |
| 25 | Tue 4 Feb 2020 | 2-2 v Birmingham CityBirmingham City 2-2 Coventry City | Emirates FA Cup Fourth Round Replay |
| 26 | Tue 11 Feb 2020 | 1-0 v PortsmouthCoventry City 1-0 Portsmouth | Sky Bet League One |
| 27 | Sat 15 Feb 2020 | 2-0 v Southend UnitedSouthend United 0-2 Coventry City | Sky Bet League One |
| 28 | Sat 22 Feb 2020 | 2-1 v RochdaleRochdale 1-2 Coventry City | Sky Bet League One |
| 29 | Tue 25 Feb 2020 | 1-1 v Rotherham UnitedCoventry City 1-1 Rotherham United | Sky Bet League One |
| 30 | Sun 1 Mar 2020 | 1-0 v SunderlandCoventry City 1-0 Sunderland | Sky Bet League One |
| 31 | Sat 7 Mar 2020 | 1-0 v Ipswich TownIpswich Town 0-1 Coventry City | Sky Bet League One |
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