| 1 | Thu 21 Mar 2019 | 5-0 v San MarinoCyprus 5-0 San Marino | European Championship Qualification Group I |
| 2 | Tue 27 Aug 2019 | 241-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 3 | Sat 31 Aug 2019 | 240-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 4 | Sat 14 Sep 2019 | 243-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 5 | Sat 5 Oct 2019 | 241-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 6 | Sat 12 Oct 2019 | 241-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 7 | Fri 18 Oct 2019 | 241-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 8 | Sat 26 Oct 2019 | 241-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 9 | Sat 16 Nov 2019 | 6 1-2 v ScotlandCyprus 1-2 Scotland | European Championship Qualification Group I |
| 10 | Tue 3 Dec 2019 | 24 1-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
| 11 | Sat 7 Dec 2019 | 242-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 12 | Sat 14 Dec 2019 | 242-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
| 13 | Sat 21 Dec 2019 | 242-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 14 | Thu 26 Dec 2019 | 242-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 15 | Wed 1 Jan 2020 | 241-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 16 | Sat 11 Jan 2020 | 24 0-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
| 17 | Sat 18 Jan 2020 | 242-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
| 18 | Sat 1 Feb 2020 | 24 2-1 v Lincoln CitySouthend United 2-1 Lincoln City | Sky Bet League One |
| 19 | Sat 8 Feb 2020 | 241-2 v BlackpoolBlackpool 2-1 Southend United | Sky Bet League One |
| 20 | Tue 11 Feb 2020 | 24 0-4 v Peterborough UnitedPeterborough United 4-0 Southend United | Sky Bet League One |
| 21 | Sat 7 Mar 2020 | 24 3-1 v Bristol RoversSouthend United 3-1 Bristol Rovers | Sky Bet League One |
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