| 1 | Sat 3 Aug 2019 | 10-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 11-3 v BlackpoolSouthend United 1-3 Blackpool | Sky Bet League One |
| 3 | Sat 31 Aug 2019 | 10-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 4 | Tue 3 Sep 2019 | 10-2 v Leyton OrientLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 5 | Sat 14 Sep 2019 | 13-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 6 | Tue 17 Sep 2019 | 13-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
| 7 | Sat 21 Sep 2019 | 11-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
| 8 | Sat 28 Sep 2019 | 10-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
| 9 | Sat 5 Oct 2019 | 11-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 10 | Sat 12 Oct 2019 | 11-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 11 | Sat 26 Oct 2019 | 11-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 12 | Thu 26 Dec 2019 | 12-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 13 | Wed 1 Jan 2020 | 11-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 14 | Sat 11 Jan 2020 | 10-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
| 15 | Sat 18 Jan 2020 | 12-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
| 16 | Sat 1 Feb 2020 | 12-1 v Lincoln CitySouthend United 2-1 Lincoln City | Sky Bet League One |
| 17 | Sat 8 Feb 2020 | 11-2 v BlackpoolBlackpool 2-1 Southend United | Sky Bet League One |
| 18 | Tue 11 Feb 2020 | 10-4 v Peterborough UnitedPeterborough United 4-0 Southend United | Sky Bet League One |
| 19 | Sat 15 Feb 2020 | 10-2 v Coventry CitySouthend United 0-2 Coventry City | Sky Bet League One |
Football Web Pages