| 2020-09-05 | Sat | EFL Cup | First round | Away | L 0–1 | Southend United | Gillingham | N | On matchday squad, but did not play | Match Report |
| 2020-09-12 | Sat | League Two | Matchweek 1 | Home | L 0–4 | Southend United | Harrogate Town FC | N | On matchday squad, but did not play | Match Report |
| 2020-09-19 | Sat | League Two | Matchweek 2 | Away | L 0–2 | Southend United | Carlisle United | N | On matchday squad, but did not play | Match Report |
| 2020-09-26 | Sat | League Two | Matchweek 3 | Home | L 1–2 | Southend United | Morecambe | N | On matchday squad, but did not play | Match Report |
| 2020-10-03 | Sat | League Two | Matchweek 4 | Away | D 1–1 | Southend United | Crawley Town | N | On matchday squad, but did not play | Match Report |
| 2020-10-10 | Sat | League Two | Matchweek 5 | Home | D 2–2 | Southend United | Exeter City | N | On matchday squad, but did not play | Match Report |
| 2020-10-17 | Sat | League Two | Matchweek 6 | Home | L 0–2 | Southend United | Cheltenham Town | N | On matchday squad, but did not play | Match Report |
| 2020-10-20 | Tue | League Two | Matchweek 7 | Away | L 0–3 | Southend United | Salford City FC | N | On matchday squad, but did not play | Match Report |
| 2020-10-24 | Sat | League Two | Matchweek 8 | Away | L 0–2 | Southend United | Tranmere Rovers | N | On matchday squad, but did not play | Match Report |
| 2020-10-27 | Tue | League Two | Matchweek 9 | Home | L 1–2 | Southend United | Oldham Athletic | N | On matchday squad, but did not play | Match Report |
| 2020-10-31 | Sat | League Two | Matchweek 10 | Home | L 0–2 | Southend United | Port Vale | N | On matchday squad, but did not play | Match Report |
| 2020-11-03 | Tue | League Two | Matchweek 11 | Away | L 0–3 | Southend United | Bradford City | N | On matchday squad, but did not play | Match Report |
| 2020-11-07 | Sat | FA Cup | First round proper | Away | D 3 (3)–3 (4) | Southend United | Boreham Wood | N | On matchday squad, but did not play | Match Report |
| 2020-11-14 | Sat | League Two | Matchweek 12 | Away | W 1–0 | Southend United | Walsall | N | On matchday squad, but did not play | Match Report |
| 2020-11-24 | Tue | League Two | Matchweek 14 | Home | L 0–1 | Southend United | Forest Green Rovers | N | On matchday squad, but did not play | Match Report |
| 2020-11-28 | Sat | League Two | Matchweek 15 | Away | L 0–3 | Southend United | Bolton Wanderers | N | On matchday squad, but did not play | Match Report |
| 2020-12-05 | Sat | League Two | Matchweek 16 | Away | D 0–0 | Southend United | Stevenage | N | On matchday squad, but did not play | Match Report |
| 2020-12-12 | Sat | League Two | Matchweek 17 | Home | W 1–0 | Southend United | Scunthorpe United | N | On matchday squad, but did not play | Match Report |
| 2020-12-15 | Tue | League Two | Matchweek 18 | Home | W 3–1 | Southend United | Grimsby Town | N | On matchday squad, but did not play | Match Report |
| 2020-12-19 | Sat | League Two | Matchweek 19 | Away | D 1–1 | Southend United | Mansfield Town | N | On matchday squad, but did not play | Match Report |
| 2020-12-26 | Sat | League Two | Matchweek 20 | Home | W 2–0 | Southend United | Colchester United | N | On matchday squad, but did not play | Match Report |
| 2020-12-29 | Tue | League Two | Matchweek 21 | Away | L 0–2 | Southend United | Leyton Orient | N | On matchday squad, but did not play | Match Report |
| 2021-01-09 | Sat | League Two | Matchweek 23 | Home | W 1–0 | Southend United | Barrow | N | On matchday squad, but did not play | Match Report |
| 2021-01-16 | Sat | League Two | Matchweek 24 | Away | D 0–0 | Southend United | Grimsby Town | N | On matchday squad, but did not play | Match Report |
| 2021-01-19 | Tue | League Two | Matchweek 13 | Home | L 1–2 | Southend United | Cambridge United | N | On matchday squad, but did not play | Match Report |
| 2021-01-23 | Sat | League Two | Matchweek 25 | Home | L 0–1 | Southend United | Mansfield Town | N | On matchday squad, but did not play | Match Report |
| 2021-01-26 | Tue | League Two | Matchweek 26 | Home | L 1–3 | Southend United | Bradford City | N | On matchday squad, but did not play | Match Report |
| 2021-01-30 | Sat | League Two | Matchweek 27 | Away | L 1–5 | Southend United | Port Vale | N | On matchday squad, but did not play | Match Report |
| 2021-02-09 | Tue | League Two | Matchweek 22 | Away | W 1–0 | Southend United | Newport County | N | On matchday squad, but did not play | Match Report |
| 2021-02-13 | Sat | League Two | Matchweek 29 | Away | D 0–0 | Southend United | Cambridge United | N | On matchday squad, but did not play | Match Report |
| 2021-02-20 | Sat | League Two | Matchweek 30 | Home | L 0–1 | Southend United | Bolton Wanderers | N | On matchday squad, but did not play | Match Report |
| 2021-02-24 | Wed | League Two | Matchweek 31 | Away | W 3–1 | Southend United | Forest Green Rovers | N | On matchday squad, but did not play | Match Report |
| 2021-02-27 | Sat | League Two | Matchweek 32 | Home | D 0–0 | Southend United | Salford City FC | N | | 45 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | | | 0 | | | | | Match Report |
| 2021-03-02 | Tue | League Two | Matchweek 33 | Away | L 0–1 | Southend United | Cheltenham Town | N | On matchday squad, but did not play | Match Report |
| 2021-03-06 | Sat | League Two | Matchweek 34 | Away | D 0–0 | Southend United | Oldham Athletic | N | On matchday squad, but did not play | Match Report |
| 2021-03-09 | Tue | League Two | Matchweek 35 | Home | L 0–2 | Southend United | Tranmere Rovers | N | On matchday squad, but did not play | Match Report |
| 2021-03-13 | Sat | League Two | Matchweek 36 | Home | D 0–0 | Southend United | Stevenage | N | On matchday squad, but did not play | Match Report |
| 2021-03-20 | Sat | League Two | Matchweek 37 | Away | D 1–1 | Southend United | Scunthorpe United | N | On matchday squad, but did not play | Match Report |
| 2021-03-23 | Tue | League Two | Matchweek 28 | Home | D 0–0 | Southend United | Walsall | N | On matchday squad, but did not play | Match Report |
| 2021-03-27 | Sat | League Two | Matchweek 38 | Away | W 1–0 | Southend United | Harrogate Town FC | N | On matchday squad, but did not play | Match Report |
| 2021-04-03 | Sat | League Two | Matchweek 39 | Home | L 0–2 | Southend United | Carlisle United | N | On matchday squad, but did not play | Match Report |
| 2021-04-06 | Tue | League Two | Matchweek 40 | Away | D 1–1 | Southend United | Morecambe | N | On matchday squad, but did not play | Match Report |
| 2021-04-10 | Sat | League Two | Matchweek 41 | Home | D 0–0 | Southend United | Crawley Town | N | On matchday squad, but did not play | Match Report |
| 2021-04-17 | Sat | League Two | Matchweek 42 | Away | D 0–0 | Southend United | Exeter City | N | On matchday squad, but did not play | Match Report |
| 2021-04-20 | Tue | League Two | Matchweek 43 | Away | L 0–2 | Southend United | Colchester United | N | On matchday squad, but did not play | Match Report |
| 2021-04-24 | Sat | League Two | Matchweek 44 | Home | W 2–1 | Southend United | Leyton Orient | N | On matchday squad, but did not play | Match Report |
| 2021-05-01 | Sat | League Two | Matchweek 45 | Away | W 2–1 | Southend United | Barrow | N | On matchday squad, but did not play | Match Report |
| 2021-05-08 | Sat | League Two | Matchweek 46 | Home | D 1–1 | Southend United | Newport County | N | On matchday squad, but did not play | Match Report |
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