| 1 | Tue 2 Sep 2014 | 222-2 v AFC WimbledonAFC Wimbledon 2-2 Southend United | Johnstone's Paint Trophy Southern Area First Round |
| 2 | Sat 13 Sep 2014 | 222-0 v PortsmouthSouthend United 2-0 Portsmouth | Sky Bet League Two |
| 3 | Tue 16 Sep 2014 | 221-0 v Cheltenham TownCheltenham Town 0-1 Southend United | Sky Bet League Two |
| 4 | Sat 20 Sep 2014 | 223-2 v York CityYork City 2-3 Southend United | Sky Bet League Two |
| 5 | Sat 27 Sep 2014 | 221-0 v Shrewsbury TownSouthend United 1-0 Shrewsbury Town | Sky Bet League Two |
| 6 | Sat 4 Oct 2014 | 220-1 v MorecambeSouthend United 0-1 Morecambe | Sky Bet League Two |
| 7 | Sat 11 Oct 2014 | 220-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League Two |
| 8 | Sat 18 Oct 2014 | 221-1 v Exeter CitySouthend United 1-1 Exeter City | Sky Bet League Two |
| 9 | Tue 21 Oct 2014 | 220-1 v Newport CountyNewport County 1-0 Southend United | Sky Bet League Two |
| 10 | Sat 25 Oct 2014 | 221-1 v BurySouthend United 1-1 Bury | Sky Bet League Two |
| 11 | Sat 1 Nov 2014 | 222-1 v Mansfield TownMansfield Town 1-2 Southend United | Sky Bet League Two |
| 12 | Sat 8 Nov 2014 | 221-2 v ChesterSouthend United 1-2 Chester | FA Cup First Round |
| 13 | Sat 29 Nov 2014 | 222-0 v Northampton TownSouthend United 2-0 Northampton Town | Sky Bet League Two |
| 14 | Sat 13 Dec 2014 | 221-4 v Wycombe WanderersWycombe Wanderers 4-1 Southend United | Sky Bet League Two |
| 15 | Sat 10 Jan 2015 | 220-0 v Plymouth ArgyleSouthend United 0-0 Plymouth Argyle | Sky Bet League Two |
| 16 | Sat 17 Jan 2015 | 223-2 v Oxford UnitedOxford United 2-3 Southend United | Sky Bet League Two |
| 17 | Sat 21 Feb 2015 | 222-4 v StevenageStevenage 4-2 Southend United | Sky Bet League Two |
| 18 | Sat 14 Mar 2015 | 223-1 v Dagenham & RedbridgeDagenham & Redbridge 1-3 Southend United | Sky Bet League Two |
| 19 | Sat 11 Apr 2015 | 221-0 v Tranmere RoversSouthend United 1-0 Tranmere Rovers | Sky Bet League Two |
| 20 | Tue 14 Apr 2015 | 222-0 v Newport CountySouthend United 2-0 Newport County | Sky Bet League Two |
| 21 | Sat 18 Apr 2015 | 221-0 v Exeter CityExeter City 0-1 Southend United | Sky Bet League Two |
| 22 | Tue 21 Apr 2015 | 221-0 v BuryBury 0-1 Southend United | Sky Bet League Two |
| 23 | Sat 25 Apr 2015 | 221-0 v Luton TownSouthend United 1-0 Luton Town | Sky Bet League Two |
| 24 | Sat 2 May 2015 | 221-3 v MorecambeMorecambe 3-1 Southend United | Sky Bet League Two |
| 25 | Sun 10 May 2015 | 221-1 v StevenageStevenage 1-1 Southend United | Sky Bet League Two Play-off Semi Final |
| 26 | Thu 14 May 2015 | 223-1 v StevenageSouthend United 3-1 Stevenage | Sky Bet League Two Play-off Semi Final |
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