| 03 Aug 2019 |
Coventry City v Southend United |
L |
1-0
|
League One |
| 10 Aug 2019 |
Southend United v Blackpool |
L |
1-3
|
League One |
| 13 Aug 2019 |
Stevenage v Southend United |
W |
1-2
|
League Cup |
| 17 Aug 2019 |
Lincoln City v Southend United |
L |
4-0
|
League One |
| 20 Aug 2019 |
Southend United v Peterborough United |
L |
0-2
|
League One |
| 24 Aug 2019 |
Wycombe Wanderers v Southend United |
L |
4-3
|
League One |
| 27 Aug 2019 |
Southend United v Milton Keynes Dons |
L |
1-4
|
League Cup |
| 31 Aug 2019 |
Southend United v Rochdale |
L |
0-3
|
League One |
| 03 Sep 2019 |
Leyton Orient v Southend United |
L |
2-0
|
Football League Trophy |
| 14 Sep 2019 |
Southend United v Fleetwood Town |
D |
3-3
|
League One |
| 17 Sep 2019 |
Shrewsbury Town v Southend United |
L |
4-3
|
League One |
| 21 Sep 2019 |
Milton Keynes Dons v Southend United |
W |
0-1
|
League One |
| 28 Sep 2019 |
Southend United v Accrington Stanley |
L |
0-1
|
League One |
| 01 Oct 2019 |
Southend United v Brighton and Hove Albion |
L |
0-2
|
Football League Trophy |
| 05 Oct 2019 |
Gillingham v Southend United |
L |
3-1
|
League One |
| 12 Oct 2019 |
Southend United v AFC Wimbledon |
L |
1-4
|
League One |
| 18 Oct 2019 |
Tranmere Rovers v Southend United |
D |
1-1
|
League One |
| 22 Oct 2019 |
Southend United v Doncaster Rovers |
L |
1-7
|
League One |
| 26 Oct 2019 |
Southend United v Ipswich Town |
L |
1-3
|
League One |
| 02 Nov 2019 |
Sunderland v Southend United |
L |
1-0
|
League One |
| 05 Nov 2019 |
Portsmouth v Southend United |
L |
4-1
|
League One |
| 10 Nov 2019 |
Dover Athletic v Southend United |
L |
1-0
|
FA Cup |
| 13 Nov 2019 |
Southend United v AFC Wimbledon |
W |
3-1
|
Football League Trophy |
| 23 Nov 2019 |
Southend United v Oxford United |
L |
0-4
|
League One |
| 03 Dec 2019 |
Burton Albion v Southend United |
D |
1-1
|
League One |
| 07 Dec 2019 |
Bristol Rovers v Southend United |
L |
4-2
|
League One |
| 14 Dec 2019 |
Southend United v Rotherham United |
D |
2-2
|
League One |
| 21 Dec 2019 |
Bolton Wanderers v Southend United |
L |
3-2
|
League One |
| 26 Dec 2019 |
Southend United v Milton Keynes Dons |
D |
2-2
|
League One |
| 01 Jan 2020 |
AFC Wimbledon v Southend United |
D |
1-1
|
League One |
| 11 Jan 2020 |
Southend United v Tranmere Rovers |
D |
0-0
|
League One |
| 18 Jan 2020 |
Accrington Stanley v Southend United |
W |
1-2
|
League One |
| 28 Jan 2020 |
Doncaster Rovers v Southend United |
L |
3-1
|
League One |
| 01 Feb 2020 |
Southend United v Lincoln City |
W |
2-1
|
League One |
| 08 Feb 2020 |
Blackpool v Southend United |
L |
2-1
|
League One |
| 11 Feb 2020 |
Peterborough United v Southend United |
L |
4-0
|
League One |
| 15 Feb 2020 |
Southend United v Coventry City |
L |
0-2
|
League One |
| 18 Feb 2020 |
Southend United v Gillingham |
L |
0-1
|
League One |
| 22 Feb 2020 |
Southend United v Burton Albion |
L |
2-3
|
League One |
| 29 Feb 2020 |
Oxford United v Southend United |
L |
2-1
|
League One |
| 07 Mar 2020 |
Southend United v Bristol Rovers |
W |
3-1
|
League One |
