| 1 | Sat 8 Aug | 81 3-1 v AltrinchamAltrincham 1-3 Southend United | Enterprise National League |
| 2 | Sat 15 Aug | 811-0 v Scunthorpe UnitedSouthend United 1-0 Scunthorpe United | Enterprise National League |
| 3 | Sat 22 Aug | 813-1 v Solihull MoorsSolihull Moors 1-3 Southend United | Enterprise National League |
| 4 | Mon 31 Aug | 81 1-1 v WokingWoking 1-1 Southend United | Enterprise National League |
| 5 | Sat 5 Sep | 813-2 v Yeovil TownSouthend United 3-2 Yeovil Town | Enterprise National League |
| 6 | Sat 12 Sep | 81 2-2 v Carlisle UnitedCarlisle United 2-2 Southend United | Enterprise National League |
| 7 | Tue 15 Sep | 813-1 v TamworthSouthend United 3-1 Tamworth | Enterprise National League |
| 8 | Sat 19 Sep | 816-1 v GatesheadGateshead 1-6 Southend United | Enterprise National League |
| 9 | Sat 26 Sep | 812-4 v BarrowSouthend United 2-4 Barrow | Enterprise National League |
| 10 | Wed 30 Sep | 81 1-1 v EastleighEastleigh 1-1 Southend United | Enterprise National League |
| 11 | Sat 3 Oct | 813-1 v AFC FyldeSouthend United 3-1 AFC Fylde | Enterprise National League |
| 12 | Sat 10 Oct | 812-1 v Boston UnitedBoston United 1-2 Southend United | Enterprise National League |
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