| 09 Aug 2008 |
Southend United v Peterborough United |
W |
1-0
|
League One |
| 12 Aug 2008 |
Southend United v Cheltenham Town |
L |
0-1
|
League Cup |
| 16 Aug 2008 |
Millwall v Southend United |
D |
1-1
|
League One |
| 22 Aug 2008 |
Southend United v Brighton and Hove Albion |
L |
0-2
|
League One |
| 30 Aug 2008 |
Walsall v Southend United |
L |
5-2
|
League One |
| 02 Sep 2008 |
Southend United v Leyton Orient |
L |
2-4
|
Johnstones Paint Trophy |
| 06 Sep 2008 |
Carlisle United v Southend United |
L |
2-1
|
League One |
| 13 Sep 2008 |
Southend United v Hereford United |
W |
1-0
|
League One |
| 20 Sep 2008 |
Crewe Alexandra v Southend United |
W |
3-4
|
League One |
| 26 Sep 2008 |
Southend United v Leyton Orient |
W |
3-0
|
League One |
| 04 Oct 2008 |
Yeovil Town v Southend United |
W |
1-2
|
League One |
| 11 Oct 2008 |
Southend United v Stockport County |
D |
1-1
|
League One |
| 18 Oct 2008 |
Southend United v Swindon Town |
W |
2-1
|
League One |
| 21 Oct 2008 |
Scunthorpe United v Southend United |
D |
1-1
|
League One |
| 25 Oct 2008 |
Bristol Rovers v Southend United |
L |
4-2
|
League One |
| 28 Oct 2008 |
Southend United v Leeds United |
W |
1-0
|
League One |
| 01 Nov 2008 |
Southend United v Colchester United |
D |
3-3
|
League One |
| 08 Nov 2008 |
AFC Telford United v Southend United |
D |
2-2
|
FA Cup |
| 15 Nov 2008 |
Tranmere Rovers v Southend United |
D |
2-2
|
League One |
| 18 Nov 2008 |
Southend United v AFC Telford United |
W |
2-0
|
FA Cup |
| 22 Nov 2008 |
Southend United v Oldham Athletic |
L |
1-2
|
League One |
| 25 Nov 2008 |
Cheltenham Town v Southend United |
D |
0-0
|
League One |
| 29 Nov 2008 |
Southend United v Luton Town |
W |
3-1
|
FA Cup |
| 06 Dec 2008 |
Leicester City v Southend United |
L |
3-0
|
League One |
| 13 Dec 2008 |
Southend United v Huddersfield Town |
L |
0-1
|
League One |
| 19 Dec 2008 |
Hartlepool United v Southend United |
L |
3-0
|
League One |
| 26 Dec 2008 |
Southend United v Northampton Town |
W |
1-0
|
League One |
| 28 Dec 2008 |
Milton Keynes Dons v Southend United |
L |
2-0
|
League One |
| 03 Jan 2009 |
Chelsea v Southend United |
D |
1-1
|
FA Cup |
| 14 Jan 2009 |
Southend United v Chelsea |
L |
1-4
|
FA Cup |
| 17 Jan 2009 |
Stockport County v Southend United |
L |
3-1
|
League One |
| 20 Jan 2009 |
Leyton Orient v Southend United |
D |
1-1
|
League One |
| 24 Jan 2009 |
Southend United v Yeovil Town |
L |
0-1
|
League One |
| 27 Jan 2009 |
Leeds United v Southend United |
L |
2-0
|
League One |
| 31 Jan 2009 |
Southend United v Bristol Rovers |
W |
1-0
|
League One |
| 14 Feb 2009 |
Southend United v Tranmere Rovers |
W |
2-1
|
League One |
| 17 Feb 2009 |
Southend United v Crewe Alexandra |
L |
0-1
|
League One |
| 21 Feb 2009 |
Colchester United v Southend United |
W |
0-1
|
League One |
| 24 Feb 2009 |
Southend United v Scunthorpe United |
W |
2-0
|
League One |
| 28 Feb 2009 |
Peterborough United v Southend United |
W |
1-2
|
League One |
| 03 Mar 2009 |
Southend United v Millwall |
L |
0-1
|
League One |
| 07 Mar 2009 |
Southend United v Walsall |
W |
2-0
|
League One |
| 10 Mar 2009 |
Brighton and Hove Albion v Southend United |
W |
1-3
|
League One |
| 14 Mar 2009 |
Hereford United v Southend United |
W |
0-1
|
League One |
| 17 Mar 2009 |
Swindon Town v Southend United |
L |
3-0
|
League One |
| 21 Mar 2009 |
Southend United v Carlisle United |
W |
3-0
|
League One |
| 27 Mar 2009 |
Southend United v Hartlepool United |
W |
3-2
|
League One |
| 04 Apr 2009 |
Huddersfield Town v Southend United |
W |
0-1
|
League One |
| 10 Apr 2009 |
Southend United v Milton Keynes Dons |
L |
0-2
|
League One |
| 13 Apr 2009 |
Northampton Town v Southend United |
W |
2-3
|
League One |
| 18 Apr 2009 |
Southend United v Leicester City |
L |
0-2
|
League One |
| 25 Apr 2009 |
Oldham Athletic v Southend United |
D |
1-1
|
League One |
| 02 May 2009 |
Southend United v Cheltenham Town |
W |
2-0
|
League One |
