| 1 | Sat 9 Aug 2014 | 161-0 v Accrington StanleyAccrington Stanley 0-1 Southend United | Sky Bet League Two |
| 2 | Tue 12 Aug 2014 | 161-2 v WalsallSouthend United 1-2 Walsall | Capital One Cup First Round |
| 3 | Sat 16 Aug 2014 | 162-0 v StevenageSouthend United 2-0 Stevenage | Sky Bet League Two |
| 4 | Tue 19 Aug 2014 | 160-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Sat 23 Aug 2014 | 161-1 v Carlisle UnitedCarlisle United 1-1 Southend United | Sky Bet League Two |
| 6 | Sat 30 Aug 2014 | 160-2 v Plymouth ArgylePlymouth Argyle 2-0 Southend United | Sky Bet League Two |
| 7 | Sat 6 Sep 2014 | 161-1 v Oxford UnitedSouthend United 1-1 Oxford United | Sky Bet League Two |
| 8 | Tue 16 Sep 2014 | 161-0 v Cheltenham TownCheltenham Town 0-1 Southend United | Sky Bet League Two |
| 9 | Sat 20 Sep 2014 | 163-2 v York CityYork City 2-3 Southend United | Sky Bet League Two |
| 10 | Sat 27 Sep 2014 | 161-0 v Shrewsbury TownSouthend United 1-0 Shrewsbury Town | Sky Bet League Two |
| 11 | Sat 4 Oct 2014 | 160-1 v MorecambeSouthend United 0-1 Morecambe | Sky Bet League Two |
| 12 | Sat 11 Oct 2014 | 160-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League Two |
| 13 | Sat 22 Nov 2014 | 162-1 v Tranmere RoversTranmere Rovers 1-2 Southend United | Sky Bet League Two |
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