| 1 | Sat 9 Aug 2014 | 11-0 v Accrington StanleyAccrington Stanley 0-1 Southend United | Sky Bet League Two |
| 2 | Sat 16 Aug 2014 | 12-0 v StevenageSouthend United 2-0 Stevenage | Sky Bet League Two |
| 3 | Tue 19 Aug 2014 | 10-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League Two |
| 4 | Sat 23 Aug 2014 | 11-1 v Carlisle UnitedCarlisle United 1-1 Southend United | Sky Bet League Two |
| 5 | Sat 30 Aug 2014 | 10-2 v Plymouth ArgylePlymouth Argyle 2-0 Southend United | Sky Bet League Two |
| 6 | Tue 2 Sep 2014 | 12-2 v AFC WimbledonAFC Wimbledon 2-2 Southend United | Johnstone's Paint Trophy Southern Area First Round |
| 7 | Sat 6 Sep 2014 | 11-1 v Oxford UnitedSouthend United 1-1 Oxford United | Sky Bet League Two |
| 8 | Sat 13 Sep 2014 | 12-0 v PortsmouthSouthend United 2-0 Portsmouth | Sky Bet League Two |
| 9 | Tue 16 Sep 2014 | 11-0 v Cheltenham TownCheltenham Town 0-1 Southend United | Sky Bet League Two |
| 10 | Sat 20 Sep 2014 | 13-2 v York CityYork City 2-3 Southend United | Sky Bet League Two |
| 11 | Sat 27 Sep 2014 | 11-0 v Shrewsbury TownSouthend United 1-0 Shrewsbury Town | Sky Bet League Two |
| 12 | Sat 4 Oct 2014 | 10-1 v MorecambeSouthend United 0-1 Morecambe | Sky Bet League Two |
| 13 | Sat 11 Oct 2014 | 10-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League Two |
| 14 | Sat 18 Oct 2014 | 11-1 v Exeter CitySouthend United 1-1 Exeter City | Sky Bet League Two |
| 15 | Tue 21 Oct 2014 | 10-1 v Newport CountyNewport County 1-0 Southend United | Sky Bet League Two |
| 16 | Sat 25 Oct 2014 | 11-1 v BurySouthend United 1-1 Bury | Sky Bet League Two |
| 17 | Sat 1 Nov 2014 | 12-1 v Mansfield TownMansfield Town 1-2 Southend United | Sky Bet League Two |
| 18 | Sat 8 Nov 2014 | 11-2 v ChesterSouthend United 1-2 Chester | FA Cup First Round |
| 19 | Sat 15 Nov 2014 | 11-0 v Hartlepool UnitedSouthend United 1-0 Hartlepool United | Sky Bet League Two |
| 20 | Sat 22 Nov 2014 | 12-1 v Tranmere RoversTranmere Rovers 1-2 Southend United | Sky Bet League Two |
| 21 | Sat 29 Nov 2014 | 12-0 v Northampton TownSouthend United 2-0 Northampton Town | Sky Bet League Two |
| 22 | Sat 13 Dec 2014 | 11-4 v Wycombe WanderersWycombe Wanderers 4-1 Southend United | Sky Bet League Two |
| 23 | Fri 19 Dec 2014 | 10-0 v Burton AlbionSouthend United 0-0 Burton Albion | Sky Bet League Two |
| 24 | Fri 26 Dec 2014 | 11-0 v Cambridge UnitedCambridge United 0-1 Southend United | Sky Bet League Two |
| 25 | Sun 28 Dec 2014 | 10-0 v Dagenham & RedbridgeSouthend United 0-0 Dagenham & Redbridge | Sky Bet League Two |
| 26 | Sat 3 Jan 2015 | 11-1 v Northampton TownNorthampton Town 1-1 Southend United | Sky Bet League Two |
| 27 | Sat 10 Jan 2015 | 10-0 v Plymouth ArgyleSouthend United 0-0 Plymouth Argyle | Sky Bet League Two |
| 28 | Sat 17 Jan 2015 | 13-2 v Oxford UnitedOxford United 2-3 Southend United | Sky Bet League Two |
| 29 | Sat 24 Jan 2015 | 12-1 v PortsmouthPortsmouth 1-2 Southend United | Sky Bet League Two |
| 30 | Sat 31 Jan 2015 | 11-0 v York CitySouthend United 1-0 York City | Sky Bet League Two |
| 31 | Sat 7 Feb 2015 | 11-1 v Shrewsbury TownShrewsbury Town 1-1 Southend United | Sky Bet League Two |
| 32 | Tue 10 Feb 2015 | 12-0 v Cheltenham TownSouthend United 2-0 Cheltenham Town | Sky Bet League Two |
| 33 | Sat 21 Feb 2015 | 12-4 v StevenageStevenage 4-2 Southend United | Sky Bet League Two |
| 34 | Sat 14 Mar 2015 | 13-1 v Dagenham & RedbridgeDagenham & Redbridge 1-3 Southend United | Sky Bet League Two |
| 35 | Wed 18 Mar 2015 | 11-2 v Burton AlbionBurton Albion 2-1 Southend United | Sky Bet League Two |
| 36 | Sat 21 Mar 2015 | 10-0 v Cambridge UnitedSouthend United 0-0 Cambridge United | Sky Bet League Two |
| 37 | Fri 3 Apr 2015 | 12-0 v Mansfield TownSouthend United 2-0 Mansfield Town | Sky Bet League Two |
| 38 | Mon 6 Apr 2015 | 11-0 v Hartlepool UnitedHartlepool United 0-1 Southend United | Sky Bet League Two |
| 39 | Sat 11 Apr 2015 | 11-0 v Tranmere RoversSouthend United 1-0 Tranmere Rovers | Sky Bet League Two |
| 40 | Tue 14 Apr 2015 | 12-0 v Newport CountySouthend United 2-0 Newport County | Sky Bet League Two |
| 41 | Sat 18 Apr 2015 | 11-0 v Exeter CityExeter City 0-1 Southend United | Sky Bet League Two |
| 42 | Tue 21 Apr 2015 | 11-0 v BuryBury 0-1 Southend United | Sky Bet League Two |
| 43 | Sat 25 Apr 2015 | 11-0 v Luton TownSouthend United 1-0 Luton Town | Sky Bet League Two |
| 44 | Sat 2 May 2015 | 11-3 v MorecambeMorecambe 3-1 Southend United | Sky Bet League Two |
| 45 | Sun 10 May 2015 | 11-1 v StevenageStevenage 1-1 Southend United | Sky Bet League Two Play-off Semi Final |
| 46 | Thu 14 May 2015 | 13-1 v StevenageSouthend United 3-1 Stevenage | Sky Bet League Two Play-off Semi Final |
| 47 | Sat 23 May 2015 | 11-1 v Wycombe WanderersSouthend United 1-1 Wycombe Wanderers | Sky Bet League Two Play-off Final |
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