Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 04/08/2018 | Southend | 2 | 3 | Doncaster | C Hicks |
| 11/08/2018 | Plymouth | 1 | 1 | Southend | J Busby |
| 18/08/2018 | Southend | 2 | 0 | Bradford | T Nield |
| 21/08/2018 | Luton | 2 | 0 | Southend | T Kettle |
| 25/08/2018 | Bristol Rvs | 0 | 1 | Southend | R Joyce |
| 01/09/2018 | Southend | 1 | 2 | Charlton | B Huxtable |
| 08/09/2018 | Southend | 2 | 3 | Peterboro | K Johnson |
| 15/09/2018 | Shrewsbury | 2 | 0 | Southend | C Sarginson |
| 22/09/2018 | Southend | 1 | 0 | Fleetwood Town | C Breakspear |
| 29/09/2018 | Wycombe | 2 | 3 | Southend | T Nield |
| 02/10/2018 | Burton | 1 | 2 | Southend | S Stockbridge |
| 06/10/2018 | Southend | 0 | 0 | Oxford | C Hicks |
| 13/10/2018 | Gillingham | 0 | 2 | Southend | J Busby |
| 20/10/2018 | Southend | 1 | 2 | Coventry | D Whitestone |
| 23/10/2018 | Southend | 3 | 0 | Walsall | A Young |
| 27/10/2018 | Sunderland | 3 | 0 | Southend | R Lewis |
| 03/11/2018 | Barnsley | 1 | 0 | Southend | B Huxtable |
| 17/11/2018 | Southend | 1 | 2 | Blackpool | N Kinseley |
| 24/11/2018 | AFC Wimbledon | 2 | 1 | Southend | S Martin |
| 27/11/2018 | Southend | 2 | 0 | Scunthorpe | T Kettle |
| 08/12/2018 | Portsmouth | 2 | 0 | Southend | L Collins |
| 15/12/2018 | Southend | 3 | 0 | Accrington | A Coggins |
| 22/12/2018 | Southend | 1 | 2 | Rochdale | N Hair |
| 26/12/2018 | Oxford | 0 | 1 | Southend | T Robinson |
| 29/12/2018 | Coventry | 1 | 0 | Southend | K Johnson |
| 01/01/2019 | Southend | 2 | 0 | Gillingham | K Stroud |
| 12/01/2019 | Southend | 2 | 3 | Plymouth | G Salisbury |
| 19/01/2019 | Bradford | 0 | 4 | Southend | M Salisbury |
| 26/01/2019 | Southend | 0 | 1 | Luton | T Bramall |
| 02/02/2019 | Southend | 1 | 2 | Bristol Rvs | O Yates |
| 09/02/2019 | Charlton | 1 | 1 | Southend | S Hooper |
| 12/02/2019 | Doncaster | 3 | 0 | Southend | A Backhouse |
| 16/02/2019 | Southend | 3 | 3 | Portsmouth | D Whitestone |
| 23/02/2019 | Accrington | 1 | 1 | Southend | E Ilderton |
| 02/03/2019 | Southend | 0 | 3 | Barnsley | K Johnson |
| 09/03/2019 | Blackpool | 2 | 2 | Southend | C Sarginson |
| 12/03/2019 | Scunthorpe | 4 | 1 | Southend | B Toner |
| 16/03/2019 | Southend | 0 | 1 | AFC Wimbledon | B Huxtable |
| 23/03/2019 | Peterboro | 2 | 0 | Southend | A Young |
| 30/03/2019 | Southend | 0 | 2 | Shrewsbury | M Salisbury |
| 06/04/2019 | Fleetwood Town | 2 | 2 | Southend | P Wright |
| 13/04/2019 | Southend | 0 | 2 | Wycombe | D Coote |
| 19/04/2019 | Walsall | 1 | 1 | Southend | R Joyce |
| 22/04/2019 | Southend | 3 | 2 | Burton | D Whitestone |
| 27/04/2019 | Rochdale | 1 | 0 | Southend | B Toner |
| 04/05/2019 | Southend | 2 | 1 | Sunderland | D Bond |