| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 12 Nov 1999 |
Lincoln City
|
4–2 |
|
H | ENG · League Two |
| 06 Nov 1999 |
York City
|
0–2 |
|
A | ENG · League Two |
| 02 Nov 1999 |
Carlisle United
|
0–1 |
|
A | ENG · League Two |
| 30 Oct 1999 |
Hereford United
|
1–0 |
|
H | ENG · FA Cup Round 1 |
| 23 Oct 1999 |
York City
|
1–1 |
|
D | ENG · League Two |
| 19 Oct 1999 |
Halifax Town
|
0–2 |
|
A | ENG · League Two |
| 16 Oct 1999 |
Brighton & Hove Albion
|
0–1 |
|
A | ENG · League Two |
| 09 Oct 1999 |
York City
|
2–1 |
|
H | ENG · League Two |
| 02 Oct 1999 |
York City
|
2–2 |
|
D | ENG · League Two |
| 25 Sep 1999 |
Hull City
|
1–1 |
|
D | ENG · League Two |
| 18 Sep 1999 |
Exeter City
|
2–1 |
|
H | ENG · League Two |
| 11 Sep 1999 |
York City
|
0–0 |
|
D | ENG · League Two |
| 04 Sep 1999 |
Rotherham United
|
1–0 |
|
H | ENG · League Two |
| 30 Aug 1999 |
York City
|
0–1 |
|
A | ENG · League Two |
| 28 Aug 1999 |
Barnet
|
6–3 |
|
H | ENG · League Two |
| 24 Aug 1999 |
Wigan Athletic
|
2–1 |
|
H | ENG · League Cup Round 1 · Leg 2 |
| 21 Aug 1999 |
York City
|
0–3 |
|
A | ENG · League Two |
| 14 Aug 1999 |
Torquay United
|
0–0 |
|
D | ENG · League Two |
| 10 Aug 1999 |
York City
|
0–1 |
|
A | ENG · League Cup Round 1 · Leg 1 |
| 07 Aug 1999 |
York City
|
1–0 |
|
H | ENG · League Two |
| 08 May 1999 |
Manchester City
|
4–0 |
|
H | ENG · League One |
| 01 May 1999 |
York City
|
0–1 |
|
A | ENG · League One |
| 27 Apr 1999 |
York City
|
1–0 |
|
H | ENG · League One |
| 24 Apr 1999 |
Macclesfield Town
|
1–2 |
|
A | ENG · League One |
| 17 Apr 1999 |
York City
|
2–2 |
|
D | ENG · League One |
| 13 Apr 1999 |
Northampton Town
|
2–2 |
|
D | ENG · League One |
| 10 Apr 1999 |
York City
|
2–1 |
|
H | ENG · League One |
| 06 Apr 1999 |
Luton Town
|
2–1 |
|
H | ENG · League One |
| 03 Apr 1999 |
York City
|
1–2 |
|
A | ENG · League One |
| 28 Mar 1999 |
Lincoln City
|
1–2 |
|
A | ENG · League One |
| 20 Mar 1999 |
York City
|
1–3 |
|
A | ENG · League One |
| 13 Mar 1999 |
Notts County
|
4–2 |
|
H | ENG · League One |
| 06 Mar 1999 |
Bristol Rovers
|
2–0 |
|
H | ENG · League One |
| 27 Feb 1999 |
York City
|
0–3 |
|
A | ENG · League One |
| 20 Feb 1999 |
Wrexham
|
1–1 |
|
D | ENG · League One |
| 13 Feb 1999 |
York City
|
1–2 |
|
A | ENG · League One |
| 05 Feb 1999 |
Colchester United
|
2–1 |
|
H | ENG · League One |
| 30 Jan 1999 |
York City
|
0–1 |
|
A | ENG · League One |
| 23 Jan 1999 |
York City
|
1–1 |
|
D | ENG · League One |
| 16 Jan 1999 |
Gillingham
|
3–1 |
|
H | ENG · League One |