| Total | Matches | Wins | Draws | Losses | |||
|---|---|---|---|---|---|---|---|
| Total | 46 | 14 | (30%) | 12 | (26%) | 20 | (43%) |
| Home | 23 | 8 | (35%) | 6 | (26%) | 9 | (39%) |
| Away | 23 | 6 | (26%) | 6 | (26%) | 11 | (48%) |
D | 1999-05-08 | Southend United |  | 1-1 |  | Hartlepool United | D46 | ||
W | 1999-05-01 | Barnet |  | 0-2 | | Southend United | D45 | ||
L | 1999-04-24 | Southend United | | 1-4 |  | Brentford | D44 | ||
W | 1999-04-17 | Plymouth Argyle |  | 0-3 | | Southend United | D43 | ||
L | 1999-04-13 | Southend United | | 0-1 |  | Cardiff City | D42 | ||
D | 1999-04-10 | Mansfield Town |  | 0-0 | | Southend United | D41 | ||
L | 1999-04-05 | Southend United | | 0-1 |  | Scunthorpe United | D40 | ||
W | 1999-04-03 | Leyton Orient |  | 0-3 | | Southend United | D39 | ||
L | 1999-03-30 | Rochdale |  | 1-0 | | Southend United | D35 | ||
L | 1999-03-26 | Southend United | | 0-1 |  | Hull City | D38 | ||
L | 1999-03-20 | Darlington |  | 2-1 | | Southend United | D37 | ||
D | 1999-03-13 | Southend United | | 0-0 |  | Exeter City | D36 | ||
W | 1999-03-06 | Southend United | | 2-0 |  | Swansea City | D34 | ||
L | 1999-02-27 | Cambridge United |  | 3-0 | | Southend United | D33 | ||
W | 1999-02-20 | Southend United | | 3-0 |  | Brighton & Hove Albion | D32 | ||
L | 1999-02-13 | Halifax Town |  | 3-1 | | Southend United | D31 | ||
D | 1999-02-06 | Rotherham |  | 2-2 | | Southend United | D30 | ||
D | 1999-01-30 | Southend United | | 0-0 |  | Torquay United | D29 | ||
L | 1999-01-23 | Southend United | | 0-1 |  | Carlisle United | D28 | ||
L | 1999-01-16 | Shrewsbury Town |  | 3-1 | | Southend United | D27 |
