| 03 Apr 1999 |
Leyton Orient
|
0–3
|
Southend United
|
A
|
ENG · League Two
|
| 26 Mar 1999 |
Halifax Town
|
1–2
|
Leyton Orient
|
A
|
ENG · League Two
|
| 20 Mar 1999 |
Scunthorpe United
|
2–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 13 Mar 1999 |
Leyton Orient
|
1–2
|
Hull City
|
A
|
ENG · League Two
|
| 06 Mar 1999 |
Leyton Orient
|
3–0
|
Rochdale
|
H
|
ENG · League Two
|
| 02 Mar 1999 |
Leyton Orient
|
2–0
|
Torquay United
|
H
|
ENG · League Two
|
| 27 Feb 1999 |
Brighton & Hove Albion
|
1–2
|
Leyton Orient
|
A
|
ENG · League Two
|
| 20 Feb 1999 |
Leyton Orient
|
2–0
|
Cambridge United
|
H
|
ENG · League Two
|
| 13 Feb 1999 |
Mansfield Town
|
1–2
|
Leyton Orient
|
A
|
ENG · League Two
|
| 06 Feb 1999 |
Carlisle United
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
| 30 Jan 1999 |
Leyton Orient
|
3–2
|
Darlington
|
H
|
ENG · League Two
|
| 23 Jan 1999 |
Bristol Rovers
|
3–0
|
Leyton Orient
|
H
|
ENG · FA Cup
Round 4
|
| 16 Jan 1999 |
Rotherham United
|
3–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 09 Jan 1999 |
Leyton Orient
|
2–2
|
Chester
|
D
|
ENG · League Two
|
| 02 Jan 1999 |
Southport
|
0–2
|
Leyton Orient
|
A
|
ENG · FA Cup
Round 3
|
| 28 Dec 1998 |
Darlington
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
| 26 Dec 1998 |
Leyton Orient
|
1–1
|
Swansea City
|
D
|
ENG · League Two
|
| 19 Dec 1998 |
Barnet
|
3–2
|
Leyton Orient
|
H
|
ENG · League Two
|
| 15 Dec 1998 |
Leyton Orient
|
2–1
|
Kingstonian
|
H
|
ENG · FA Cup
Round 2
|
| 12 Dec 1998 |
Leyton Orient
|
1–2
|
Peterborough United
|
A
|
ENG · League Two
|
| 06 Dec 1998 |
Kingstonian
|
0–0
|
Leyton Orient
|
D
|
ENG · FA Cup
Round 2
|
| 28 Nov 1998 |
Plymouth Argyle
|
2–4
|
Leyton Orient
|
A
|
ENG · League Two
|
| 21 Nov 1998 |
Leyton Orient
|
2–1
|
Brentford
|
H
|
ENG · League Two
|
| 14 Nov 1998 |
Leyton Orient
|
4–2
|
Brighton & Hove Albion
|
H
|
ENG · FA Cup
Round 1
|
| 10 Nov 1998 |
Shrewsbury Town
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
| 07 Nov 1998 |
Hull City
|
0–1
|
Leyton Orient
|
A
|
ENG · League Two
|
| 31 Oct 1998 |
Leyton Orient
|
1–0
|
Scunthorpe United
|
H
|
ENG · League Two
|
| 24 Oct 1998 |
Leyton Orient
|
1–0
|
Halifax Town
|
H
|
ENG · League Two
|
| 20 Oct 1998 |
Cardiff City
|
0–0
|
Leyton Orient
|
D
|
ENG · League Two
|
| 17 Oct 1998 |
Southend United
|
2–2
|
Leyton Orient
|
D
|
ENG · League Two
|
| 09 Oct 1998 |
Leyton Orient
|
2–0
|
Exeter City
|
H
|
ENG · League Two
|
| 03 Oct 1998 |
Leyton Orient
|
1–1
|
Hartlepool United
|
D
|
ENG · League Two
|
| 27 Sep 1998 |
Rochdale
|
2–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 22 Sep 1998 |
Nottingham Forest
|
0–0
|
Leyton Orient
|
D
|
ENG · League Cup
Round 2 · Leg 2
|
| 19 Sep 1998 |
Leyton Orient
|
1–0
|
Brighton & Hove Albion
|
H
|
ENG · League Two
|
| 15 Sep 1998 |
Leyton Orient
|
1–5
|
Nottingham Forest
|
A
|
ENG · League Cup
Round 2 · Leg 1
|
| 12 Sep 1998 |
Cambridge United
|
1–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 08 Sep 1998 |
Leyton Orient
|
1–1
|
Mansfield Town
|
D
|
ENG · League Two
|
| 05 Sep 1998 |
Leyton Orient
|
2–1
|
Carlisle United
|
H
|
ENG · League Two
|
| 01 Sep 1998 |
Torquay United
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
