| 1 | Sat 3 Aug 2013 | 41-0 v Plymouth ArgyleSouthend United 1-0 Plymouth Argyle | Sky Bet League Two |
| 2 | Sat 10 Aug 2013 | 41-0 v Hartlepool UnitedHartlepool United 0-1 Southend United | Sky Bet League Two |
| 3 | Sat 17 Aug 2013 | 42-0 v Northampton TownSouthend United 2-0 Northampton Town | Sky Bet League Two |
| 4 | Fri 1 Nov 2013 | 43-0 v Mansfield TownSouthend United 3-0 Mansfield Town | Sky Bet League Two |
| 5 | Sat 16 Nov 2013 | 42-0 v Exeter CityExeter City 0-2 Southend United | Sky Bet League Two |
| 6 | Sat 23 Nov 2013 | 42-1 v York CitySouthend United 2-1 York City | Sky Bet League Two |
| 7 | Tue 26 Nov 2013 | 42-1 v PortsmouthPortsmouth 1-2 Southend United | Sky Bet League Two |
| 8 | Sat 30 Nov 2013 | 41-1 v Cheltenham TownSouthend United 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 7 Dec 2013 | 43-1 v ChesterfieldChesterfield 1-3 Southend United | FA Cup with Budweiser Second Round |
| 10 | Sat 14 Dec 2013 | 40-1 v Torquay UnitedTorquay United 1-0 Southend United | Sky Bet League Two |
| 11 | Sat 4 Jan 2014 | 44-1 v MillwallSouthend United 4-1 Millwall | FA Cup with Budweiser Third Round |
| 12 | Sat 11 Jan 2014 | 41-1 v Plymouth ArgylePlymouth Argyle 1-1 Southend United | Sky Bet League Two |
| 13 | Sat 8 Feb 2014 | 41-2 v Mansfield TownMansfield Town 2-1 Southend United | Sky Bet League Two |
| 14 | Sat 22 Feb 2014 | 40-0 v York CityYork City 0-0 Southend United | Sky Bet League Two |
| 15 | Tue 25 Feb 2014 | 41-2 v Northampton TownNorthampton Town 2-1 Southend United | Sky Bet League Two |
| 16 | Sat 8 Mar 2014 | 41-2 v MorecambeMorecambe 2-1 Southend United | Sky Bet League Two |
| 17 | Tue 11 Mar 2014 | 42-2 v Scunthorpe UnitedScunthorpe United 2-2 Southend United | Sky Bet League Two |
| 18 | Sat 15 Mar 2014 | 40-0 v BurySouthend United 0-0 Bury | Sky Bet League Two |
| 19 | Mon 24 Mar 2014 | 43-0 v Oxford UnitedSouthend United 3-0 Oxford United | Sky Bet League Two |
| 20 | Sat 29 Mar 2014 | 41-0 v Torquay UnitedSouthend United 1-0 Torquay United | Sky Bet League Two |
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