| 1 | Tue 13 Aug 2019 | 132-1 v StevenageStevenage 1-2 Southend United | Carabao Cup First Round |
| 2 | Sat 17 Aug 2019 | 130-4 v Lincoln CityLincoln City 4-0 Southend United | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 130-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 4 | Sat 24 Aug 2019 | 13 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 5 | Tue 27 Aug 2019 | 131-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 6 | Fri 18 Oct 2019 | 131-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 7 | Tue 22 Oct 2019 | 131-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 8 | Sat 2 Nov 2019 | 130-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
| 9 | Sun 10 Nov 2019 | 130-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 10 | Wed 13 Nov 2019 | 133-1 v AFC WimbledonSouthend United 3-1 AFC Wimbledon | Leasing.com Trophy Southern Group C |
| 11 | Sat 23 Nov 2019 | 130-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
| 12 | Tue 3 Dec 2019 | 131-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
| 13 | Sat 7 Dec 2019 | 132-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 14 | Sat 14 Dec 2019 | 132-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
| 15 | Sat 21 Dec 2019 | 132-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
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