| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 08 May 1999 |
Wigan Athletic
|
3–1 |
|
H | ENG · League One |
| 03 May 1999 |
Chesterfield
|
0–0 |
|
D | ENG · League One |
| 27 Apr 1999 |
Luton Town
|
1–0 |
|
H | ENG · League One |
| 24 Apr 1999 |
Bournemouth
|
0–0 |
|
D | ENG · League One |
| 20 Apr 1999 |
Chesterfield
|
0–0 |
|
D | ENG · League One |
| 17 Apr 1999 |
Chesterfield
|
1–0 |
|
H | ENG · League One |
| 13 Apr 1999 |
Macclesfield Town
|
2–0 |
|
H | ENG · League One |
| 10 Apr 1999 |
Notts County
|
2–0 |
|
H | ENG · League One |
| 05 Apr 1999 |
Chesterfield
|
1–1 |
|
D | ENG · League One |
| 03 Apr 1999 |
York City
|
1–2 |
|
A | ENG · League One |
| 27 Mar 1999 |
Chesterfield
|
1–2 |
|
A | ENG · League One |
| 20 Mar 1999 |
Chesterfield
|
3–1 |
|
H | ENG · League One |
| 13 Mar 1999 |
Lincoln City
|
2–0 |
|
H | ENG · League One |
| 06 Mar 1999 |
Wrexham
|
0–0 |
|
D | ENG · League One |
| 02 Mar 1999 |
Chesterfield
|
2–1 |
|
H | ENG · League One |
| 27 Feb 1999 |
Chesterfield
|
1–1 |
|
D | ENG · League One |
| 20 Feb 1999 |
Walsall
|
1–1 |
|
D | ENG · League One |
| 06 Feb 1999 |
Gillingham
|
3–1 |
|
H | ENG · League One |
| 30 Jan 1999 |
Chesterfield
|
2–0 |
|
H | ENG · League One |
| 23 Jan 1999 |
Chesterfield
|
0–1 |
|
A | ENG · League One |
| 16 Jan 1999 |
Burnley
|
1–2 |
|
A | ENG · League One |
| 09 Jan 1999 |
Chesterfield
|
3–1 |
|
H | ENG · League One |
| 02 Jan 1999 |
Reading
|
1–2 |
|
A | ENG · League One |
| 28 Dec 1998 |
Wycombe Wanderers
|
1–0 |
|
H | ENG · League One |
| 26 Dec 1998 |
Chesterfield
|
1–3 |
|
A | ENG · League One |
| 19 Dec 1998 |
Chesterfield
|
1–1 |
|
D | ENG · League One |
| 12 Dec 1998 |
Northampton Town
|
1–0 |
|
H | ENG · League One |
| 05 Dec 1998 |
Blackpool
|
1–1 |
|
D | ENG · League One |
| 28 Nov 1998 |
Chesterfield
|
2–0 |
|
H | ENG · League One |
| 21 Nov 1998 |
Fulham
|
2–1 |
|
H | ENG · League One |
| 14 Nov 1998 |
Wycombe Wanderers
|
1–0 |
|
H | ENG · FA Cup Round 1 |
| 10 Nov 1998 |
Chesterfield
|
3–1 |
|
H | ENG · League One |
| 07 Nov 1998 |
Chesterfield
|
3–0 |
|
H | ENG · League One |
| 20 Oct 1998 |
Chesterfield
|
3–0 |
|
H | ENG · League One |
| 17 Oct 1998 |
Chesterfield
|
2–1 |
|
H | ENG · League One |
| 12 Oct 1998 |
Stoke City
|
0–0 |
|
D | ENG · League One |
| 03 Oct 1998 |
Millwall
|
0–0 |
|
D | ENG · League One |
| 27 Sep 1998 |
Chesterfield
|
2–1 |
|
H | ENG · League One |
| 22 Sep 1998 |
Chesterfield
|
1–3 |
|
A | ENG · League Cup Round 2 · Leg 2 |
| 19 Sep 1998 |
Manchester City
|
1–1 |
|
D | ENG · League One |