| 1 | Sat 6 Aug 2016 | 11-3 v GillinghamSouthend United 1-3 Gillingham | Sky Bet League One |
| 2 | Tue 9 Aug 2016 | 11-3 v GillinghamSouthend United 1-3 Gillingham | EFL Cup First Round |
| 3 | Sat 13 Aug 2016 | 10-2 v Port ValePort Vale 2-0 Southend United | Sky Bet League One |
| 4 | Tue 16 Aug 2016 | 13-0 v Sheffield UnitedSheffield United 0-3 Southend United | Sky Bet League One |
| 5 | Sat 20 Aug 2016 | 11-1 v Bristol RoversSouthend United 1-1 Bristol Rovers | Sky Bet League One |
| 6 | Sat 27 Aug 2016 | 10-2 v Fleetwood TownSouthend United 0-2 Fleetwood Town | Sky Bet League One |
| 7 | Sat 17 Sep 2016 | 13-1 v MillwallSouthend United 3-1 Millwall | Sky Bet League One |
| 8 | Sat 24 Sep 2016 | 10-4 v Northampton TownNorthampton Town 4-0 Southend United | Sky Bet League One |
| 9 | Tue 27 Sep 2016 | 12-1 v Oxford UnitedSouthend United 2-1 Oxford United | Sky Bet League One |
| 10 | Sat 1 Oct 2016 | 11-1 v Peterborough UnitedSouthend United 1-1 Peterborough United | Sky Bet League One |
| 11 | Sat 8 Oct 2016 | 10-3 v RochdaleRochdale 3-0 Southend United | Sky Bet League One |
| 12 | Sat 15 Oct 2016 | 11-0 v ChesterfieldSouthend United 1-0 Chesterfield | Sky Bet League One |
| 13 | Tue 18 Oct 2016 | 11-1 v Bradford CityBradford City 1-1 Southend United | Sky Bet League One |
| 14 | Sat 22 Oct 2016 | 13-0 v Milton Keynes DonsMilton Keynes Dons 0-3 Southend United | Sky Bet League One |
| 15 | Sat 29 Oct 2016 | 11-1 v Shrewsbury TownSouthend United 1-1 Shrewsbury Town | Sky Bet League One |
| 16 | Fri 4 Nov 2016 | 10-1 v MillwallMillwall 1-0 Southend United | Emirates FA Cup First Round |
| 17 | Sat 12 Nov 2016 | 14-1 v BuryBury 1-4 Southend United | Sky Bet League One |
| 18 | Sat 19 Nov 2016 | 13-0 v Bradford CitySouthend United 3-0 Bradford City | Sky Bet League One |
| 19 | Tue 22 Nov 2016 | 11-1 v Swindon TownSouthend United 1-1 Swindon Town | Sky Bet League One |
| 20 | Sat 26 Nov 2016 | 10-0 v WalsallWalsall 0-0 Southend United | Sky Bet League One |
| 21 | Tue 6 Dec 2016 | 11-1 v Oxford UnitedSouthend United 1-1 Oxford United | Checkatrade Trophy Second Round |
| 22 | Sat 10 Dec 2016 | 13-1 v Coventry CitySouthend United 3-1 Coventry City | Sky Bet League One |
| 23 | Sat 17 Dec 2016 | 12-0 v Oldham AthleticOldham Athletic 0-2 Southend United | Sky Bet League One |
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