| 1 | Sat 5 Sep | 20 3-2 v Yeovil TownSouthend United 3-2 Yeovil Town | Enterprise National League |
| 2 | Sat 12 Sep | 20 2-2 v Carlisle UnitedCarlisle United 2-2 Southend United | Enterprise National League |
| 3 | Tue 15 Sep | 203-1 v TamworthSouthend United 3-1 Tamworth | Enterprise National League |
| 4 | Sat 19 Sep | 206-1 v GatesheadGateshead 1-6 Southend United | Enterprise National League |
| 5 | Sat 26 Sep | 20 2-4 v BarrowSouthend United 2-4 Barrow | Enterprise National League |
| 6 | Wed 30 Sep | 201-1 v EastleighEastleigh 1-1 Southend United | Enterprise National League |
| 7 | Sat 3 Oct | 203-1 v AFC FyldeSouthend United 3-1 AFC Fylde | Enterprise National League |
| 8 | Sat 10 Oct | 202-1 v Boston UnitedBoston United 1-2 Southend United | Enterprise National League |
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