| 1 | Sat 9 Aug 2014 | 31-0 v Accrington StanleyAccrington Stanley 0-1 Southend United | Sky Bet League Two |
| 2 | Tue 12 Aug 2014 | 31-2 v WalsallSouthend United 1-2 Walsall | Capital One Cup First Round |
| 3 | Sat 16 Aug 2014 | 32-0 v StevenageSouthend United 2-0 Stevenage | Sky Bet League Two |
| 4 | Tue 19 Aug 2014 | 30-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Sat 23 Aug 2014 | 31-1 v Carlisle UnitedCarlisle United 1-1 Southend United | Sky Bet League Two |
| 6 | Sat 30 Aug 2014 | 30-2 v Plymouth ArgylePlymouth Argyle 2-0 Southend United | Sky Bet League Two |
| 7 | Tue 2 Sep 2014 | 32-2 v AFC WimbledonAFC Wimbledon 2-2 Southend United | Johnstone's Paint Trophy Southern Area First Round |
| 8 | Sat 6 Sep 2014 | 31-1 v Oxford UnitedSouthend United 1-1 Oxford United | Sky Bet League Two |
| 9 | Fri 19 Dec 2014 | 30-0 v Burton AlbionSouthend United 0-0 Burton Albion | Sky Bet League Two |
| 10 | Fri 26 Dec 2014 | 31-0 v Cambridge UnitedCambridge United 0-1 Southend United | Sky Bet League Two |
| 11 | Sun 28 Dec 2014 | 30-0 v Dagenham & RedbridgeSouthend United 0-0 Dagenham & Redbridge | Sky Bet League Two |
| 12 | Sat 3 Jan 2015 | 31-1 v Northampton TownNorthampton Town 1-1 Southend United | Sky Bet League Two |
| 13 | Sat 10 Jan 2015 | 30-0 v Plymouth ArgyleSouthend United 0-0 Plymouth Argyle | Sky Bet League Two |
| 14 | Sat 17 Jan 2015 | 33-2 v Oxford UnitedOxford United 2-3 Southend United | Sky Bet League Two |
| 15 | Sat 24 Jan 2015 | 32-1 v PortsmouthPortsmouth 1-2 Southend United | Sky Bet League Two |
| 16 | Sat 31 Jan 2015 | 31-0 v York CitySouthend United 1-0 York City | Sky Bet League Two |
| 17 | Sat 7 Feb 2015 | 31-1 v Shrewsbury TownShrewsbury Town 1-1 Southend United | Sky Bet League Two |
| 18 | Tue 10 Feb 2015 | 32-0 v Cheltenham TownSouthend United 2-0 Cheltenham Town | Sky Bet League Two |
| 19 | Sat 14 Feb 2015 | 31-2 v Accrington StanleySouthend United 1-2 Accrington Stanley | Sky Bet League Two |
| 20 | Sat 21 Feb 2015 | 32-4 v StevenageStevenage 4-2 Southend United | Sky Bet League Two |
| 21 | Sat 28 Feb 2015 | 32-0 v Carlisle UnitedSouthend United 2-0 Carlisle United | Sky Bet League Two |
| 22 | Tue 3 Mar 2015 | 30-0 v AFC WimbledonAFC Wimbledon 0-0 Southend United | Sky Bet League Two |
| 23 | Sat 7 Mar 2015 | 32-2 v Wycombe WanderersSouthend United 2-2 Wycombe Wanderers | Sky Bet League Two |
| 24 | Sat 14 Mar 2015 | 33-1 v Dagenham & RedbridgeDagenham & Redbridge 1-3 Southend United | Sky Bet League Two |
| 25 | Wed 18 Mar 2015 | 31-2 v Burton AlbionBurton Albion 2-1 Southend United | Sky Bet League Two |
| 26 | Sat 21 Mar 2015 | 30-0 v Cambridge UnitedSouthend United 0-0 Cambridge United | Sky Bet League Two |
| 27 | Fri 3 Apr 2015 | 32-0 v Mansfield TownSouthend United 2-0 Mansfield Town | Sky Bet League Two |
| 28 | Mon 6 Apr 2015 | 31-0 v Hartlepool UnitedHartlepool United 0-1 Southend United | Sky Bet League Two |
| 29 | Sat 11 Apr 2015 | 31-0 v Tranmere RoversSouthend United 1-0 Tranmere Rovers | Sky Bet League Two |
| 30 | Tue 14 Apr 2015 | 32-0 v Newport CountySouthend United 2-0 Newport County | Sky Bet League Two |
| 31 | Sat 18 Apr 2015 | 31-0 v Exeter CityExeter City 0-1 Southend United | Sky Bet League Two |
| 32 | Tue 21 Apr 2015 | 31-0 v BuryBury 0-1 Southend United | Sky Bet League Two |
| 33 | Sat 25 Apr 2015 | 31-0 v Luton TownSouthend United 1-0 Luton Town | Sky Bet League Two |
| 34 | Sat 2 May 2015 | 31-3 v MorecambeMorecambe 3-1 Southend United | Sky Bet League Two |
| 35 | Sun 10 May 2015 | 31-1 v StevenageStevenage 1-1 Southend United | Sky Bet League Two Play-off Semi Final |
| 36 | Thu 14 May 2015 | 33-1 v StevenageSouthend United 3-1 Stevenage | Sky Bet League Two Play-off Semi Final |
| 37 | Sat 23 May 2015 | 31-1 v Wycombe WanderersSouthend United 1-1 Wycombe Wanderers | Sky Bet League Two Play-off Final |
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