| 1 | Sat 10 Aug 2019 | 1-3 v BlackpoolSouthend United 1-3 Blackpool | Sky Bet League One |
| 2 | Tue 20 Aug 2019 | 0-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 3 | Sat 24 Aug 2019 | 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 4 | Tue 27 Aug 2019 | 1-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 5 | Sat 31 Aug 2019 | 0-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 6 | Sat 14 Sep 2019 | 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 7 | Tue 17 Sep 2019 | 3-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
| 8 | Sat 28 Sep 2019 | 0-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
| 9 | Sat 5 Oct 2019 | 1-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 10 | Fri 18 Oct 2019 | 1-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 11 | Tue 22 Oct 2019 | 1-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 12 | Sat 26 Oct 2019 | 1-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 13 | Sat 7 Dec 2019 | 2-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 14 | Sat 14 Dec 2019 | 2-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
| 15 | Sat 21 Dec 2019 | 2-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 16 | Thu 26 Dec 2019 | 2-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 17 | Wed 1 Jan 2020 | 1-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 18 | Sat 11 Jan 2020 | 0-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
Football Web Pages