| 18 Mar 2000 |
Bristol Rovers
|
3–1
|
Chesterfield
|
H
|
ENG · League One
|
| 11 Mar 2000 |
Chesterfield
|
1–1
|
Wigan Athletic
|
D
|
ENG · League One
|
| 04 Mar 2000 |
Stoke City
|
5–1
|
Chesterfield
|
H
|
ENG · League One
|
| 26 Feb 2000 |
Chesterfield
|
2–0
|
Reading
|
H
|
ENG · League One
|
| 19 Feb 2000 |
Oxford United
|
2–1
|
Chesterfield
|
H
|
ENG · League One
|
| 12 Feb 2000 |
Chesterfield
|
0–1
|
Preston North End
|
A
|
ENG · League One
|
| 05 Feb 2000 |
Bristol City
|
3–0
|
Chesterfield
|
H
|
ENG · League One
|
| 01 Feb 2000 |
Chesterfield
|
0–0
|
Gillingham
|
D
|
ENG · League One
|
| 29 Jan 2000 |
Chesterfield
|
2–0
|
Millwall
|
H
|
ENG · League One
|
| 22 Jan 2000 |
Cambridge United
|
2–0
|
Chesterfield
|
H
|
ENG · League One
|
| 15 Jan 2000 |
Chesterfield
|
1–1
|
Burnley
|
D
|
ENG · League One
|
| 08 Jan 2000 |
Chesterfield
|
1–0
|
Brentford
|
H
|
ENG · League One
|
| 03 Jan 2000 |
Wycombe Wanderers
|
3–0
|
Chesterfield
|
H
|
ENG · League One
|
| 26 Dec 1999 |
Luton Town
|
1–1
|
Chesterfield
|
D
|
ENG · League One
|
| 10 Dec 1999 |
Brentford
|
1–1
|
Chesterfield
|
D
|
ENG · League One
|
| 07 Dec 1999 |
Chesterfield
|
0–2
|
Bristol City
|
A
|
ENG · League One
|
| 03 Dec 1999 |
Colchester United
|
1–0
|
Chesterfield
|
H
|
ENG · League One
|
| 27 Nov 1999 |
Chesterfield
|
0–0
|
Oxford United
|
D
|
ENG · League One
|
| 20 Nov 1999 |
Chesterfield
|
0–1
|
Bristol Rovers
|
A
|
ENG · League One
|
| 12 Nov 1999 |
Cardiff City
|
2–1
|
Chesterfield
|
H
|
ENG · League One
|
| 06 Nov 1999 |
Chesterfield
|
0–1
|
Oldham Athletic
|
A
|
ENG · League One
|
| 02 Nov 1999 |
Wigan Athletic
|
3–0
|
Chesterfield
|
H
|
ENG · League One
|
| 30 Oct 1999 |
Chesterfield
|
1–2
|
Enfield
|
A
|
ENG · FA Cup
Round 1
|
| 23 Oct 1999 |
Chesterfield
|
1–1
|
Scunthorpe United
|
D
|
ENG · League One
|
| 19 Oct 1999 |
Notts County
|
1–0
|
Chesterfield
|
H
|
ENG · League One
|
| 16 Oct 1999 |
Wrexham
|
1–1
|
Chesterfield
|
D
|
ENG · League One
|
| 09 Oct 1999 |
Chesterfield
|
0–0
|
Blackpool
|
D
|
ENG · League One
|
| 02 Oct 1999 |
Chesterfield
|
0–1
|
Bournemouth
|
A
|
ENG · League One
|
| 25 Sep 1999 |
Scunthorpe United
|
0–0
|
Chesterfield
|
D
|
ENG · League One
|
| 21 Sep 1999 |
Middlesbrough
|
2–1
|
Chesterfield
|
H
|
ENG · League Cup
Round 2 · Leg 2
|
| 18 Sep 1999 |
Reading
|
1–0
|
Chesterfield
|
H
|
ENG · League One
|
| 14 Sep 1999 |
Chesterfield
|
0–0
|
Middlesbrough
|
D
|
ENG · League Cup
Round 2 · Leg 1
|
| 11 Sep 1999 |
Chesterfield
|
0–2
|
Stoke City
|
A
|
ENG · League One
|
| 04 Sep 1999 |
Preston North End
|
0–2
|
Chesterfield
|
A
|
ENG · League One
|
| 28 Aug 1999 |
Millwall
|
1–1
|
Chesterfield
|
D
|
ENG · League One
|
| 24 Aug 1999 |
Chesterfield
|
2–1
|
Rochdale
|
H
|
ENG · League Cup
Round 1 · Leg 2
|
| 21 Aug 1999 |
Chesterfield
|
4–2
|
Cambridge United
|
H
|
ENG · League One
|
| 14 Aug 1999 |
Burnley
|
2–1
|
Chesterfield
|
H
|
ENG · League One
|
| 10 Aug 1999 |
Rochdale
|
1–2
|
Chesterfield
|
A
|
ENG · League Cup
Round 1 · Leg 1
|
| 07 Aug 1999 |
Chesterfield
|
0–1
|
Colchester United
|
A
|
ENG · League One
|
