| 08 Jan 2000 |
Exeter City
|
1–3
|
Leyton Orient
|
A
|
ENG · League Two
|
| 03 Jan 2000 |
Leyton Orient
|
0–0
|
Hull City
|
D
|
ENG · League Two
|
| 28 Dec 1999 |
Chester
|
1–5
|
Leyton Orient
|
A
|
ENG · League Two
|
| 26 Dec 1999 |
Leyton Orient
|
0–1
|
Swansea City
|
A
|
ENG · League Two
|
| 18 Dec 1999 |
Macclesfield Town
|
1–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 04 Dec 1999 |
Leyton Orient
|
0–1
|
Carlisle United
|
A
|
ENG · League Two
|
| 27 Nov 1999 |
Cheltenham Town
|
2–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 23 Nov 1999 |
Leyton Orient
|
0–0
|
Rochdale
|
D
|
ENG · League Two
|
| 12 Nov 1999 |
Rotherham United
|
0–1
|
Leyton Orient
|
A
|
ENG · League Two
|
| 09 Nov 1999 |
Cardiff City
|
3–1
|
Leyton Orient
|
H
|
ENG · FA Cup
Round 1
|
| 06 Nov 1999 |
Leyton Orient
|
0–0
|
Northampton Town
|
D
|
ENG · League Two
|
| 02 Nov 1999 |
Darlington
|
3–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 30 Oct 1999 |
Leyton Orient
|
1–1
|
Cardiff City
|
D
|
ENG · FA Cup
Round 1
|
| 23 Oct 1999 |
Hartlepool United
|
1–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 19 Oct 1999 |
Leyton Orient
|
0–0
|
Barnet
|
D
|
ENG · League Two
|
| 16 Oct 1999 |
Leyton Orient
|
2–3
|
Lincoln City
|
A
|
ENG · League Two
|
| 09 Oct 1999 |
York City
|
2–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 02 Oct 1999 |
Plymouth Argyle
|
5–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 25 Sep 1999 |
Leyton Orient
|
2–1
|
Hartlepool United
|
H
|
ENG · League Two
|
| 21 Sep 1999 |
Leyton Orient
|
1–0
|
Grimsby Town
|
H
|
ENG · League Cup
Round 2 · Leg 2
|
| 18 Sep 1999 |
Leyton Orient
|
0–2
|
Torquay United
|
A
|
ENG · League Two
|
| 14 Sep 1999 |
Grimsby Town
|
4–1
|
Leyton Orient
|
H
|
ENG · League Cup
Round 2 · Leg 1
|
| 11 Sep 1999 |
Mansfield Town
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
| 03 Sep 1999 |
Leyton Orient
|
1–2
|
Shrewsbury Town
|
A
|
ENG · League Two
|
| 30 Aug 1999 |
Southend United
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
| 28 Aug 1999 |
Leyton Orient
|
1–0
|
Halifax Town
|
H
|
ENG · League Two
|
| 24 Aug 1999 |
Leyton Orient
|
1–1
|
Swindon Town
|
D
|
ENG · League Cup
Round 1 · Leg 2
|
| 21 Aug 1999 |
Peterborough United
|
2–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 14 Aug 1999 |
Leyton Orient
|
1–2
|
Brighton & Hove Albion
|
A
|
ENG · League Two
|
| 10 Aug 1999 |
Swindon Town
|
0–1
|
Leyton Orient
|
A
|
ENG · League Cup
Round 1 · Leg 1
|
| 07 Aug 1999 |
Carlisle United
|
2–1
|
Leyton Orient
|
H
|
ENG · League Two
|
| 08 May 1999 |
Leyton Orient
|
2–2
|
Barnet
|
D
|
ENG · League Two
|
| 01 May 1999 |
Peterborough United
|
3–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 27 Apr 1999 |
Hartlepool United
|
1–0
|
Leyton Orient
|
H
|
ENG · League Two
|
| 24 Apr 1999 |
Leyton Orient
|
6–1
|
Shrewsbury Town
|
H
|
ENG · League Two
|
| 21 Apr 1999 |
Scarborough
|
1–3
|
Leyton Orient
|
A
|
ENG · League Two
|
| 17 Apr 1999 |
Brentford
|
0–0
|
Leyton Orient
|
D
|
ENG · League Two
|
| 13 Apr 1999 |
Leyton Orient
|
4–3
|
Plymouth Argyle
|
H
|
ENG · League Two
|
| 10 Apr 1999 |
Leyton Orient
|
1–1
|
Cardiff City
|
D
|
ENG · League Two
|
| 05 Apr 1999 |
Exeter City
|
1–1
|
Leyton Orient
|
D
|
ENG · League Two
|
