| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 28 Feb 2009 |
Chesterfield
|
1–1 |
|
D | ENG · League Two |
| 20 Feb 2009 |
Chesterfield
|
1–0 |
|
H | ENG · League Two |
| 14 Feb 2009 |
Shrewsbury Town
|
2–1 |
|
H | ENG · League Two |
| 31 Jan 2009 |
Notts County
|
0–1 |
|
A | ENG · League Two |
| 28 Jan 2009 |
Chesterfield
|
2–1 |
|
H | ENG · League Two |
| 24 Jan 2009 |
Chesterfield
|
1–2 |
|
A | ENG · League Two |
| 17 Jan 2009 |
Chester
|
1–3 |
|
A | ENG · League Two |
| 03 Jan 2009 |
Ipswich Town
|
3–0 |
|
H | ENG · FA Cup Round 3 |
| 28 Dec 2008 |
Darlington
|
0–0 |
|
D | ENG · League Two |
| 26 Dec 2008 |
Chesterfield
|
2–2 |
|
D | ENG · League Two |
| 23 Dec 2008 | Droylsden | 2–1 |
|
H | ENG · FA Cup Round 2 |
| 20 Dec 2008 |
Port Vale
|
0–1 |
|
A | ENG · League Two |
| 12 Dec 2008 |
Chesterfield
|
2–4 |
|
A | ENG · League Two |
| 09 Dec 2008 |
Chesterfield
|
2–2 | Droylsden | D | ENG · FA Cup Round 2 |
| 06 Dec 2008 |
Gillingham
|
2–1 |
|
H | ENG · League Two |
| 25 Nov 2008 |
Bradford City
|
3–2 |
|
H | ENG · League Two |
| 22 Nov 2008 |
Chesterfield
|
1–1 |
|
D | ENG · League Two |
| 14 Nov 2008 |
Chesterfield
|
2–2 |
|
D | ENG · League Two |
| 08 Nov 2008 |
Chesterfield
|
3–1 |
|
H | ENG · FA Cup Round 1 |
| 01 Nov 2008 |
Bournemouth
|
1–1 |
|
D | ENG · League Two |
| 28 Oct 2008 |
Exeter City
|
1–6 |
|
A | ENG · League Two |
| 25 Oct 2008 |
Chesterfield
|
3–1 |
|
H | ENG · League Two |
| 22 Oct 2008 |
Chesterfield
|
5–1 |
|
H | ENG · League Two |
| 18 Oct 2008 |
Lincoln City
|
3–1 |
|
H | ENG · League Two |
| 11 Oct 2008 |
Chesterfield
|
1–1 |
|
D | ENG · League Two |
| 04 Oct 2008 |
Morecambe
|
2–2 |
|
D | ENG · League Two |
| 27 Sep 2008 |
Chesterfield
|
0–1 |
|
A | ENG · League Two |
| 20 Sep 2008 |
Rochdale
|
2–1 |
|
H | ENG · League Two |
| 13 Sep 2008 |
Dagenham & Redbridge
|
3–0 |
|
H | ENG · League Two |
| 06 Sep 2008 |
Chesterfield
|
1–0 |
|
H | ENG · League Two |
| 30 Aug 2008 |
Chesterfield
|
0–1 |
|
A | ENG · League Two |
| 23 Aug 2008 |
Grimsby Town
|
0–1 |
|
A | ENG · League Two |
| 16 Aug 2008 |
Chesterfield
|
1–3 |
|
A | ENG · League Two |
| 12 Aug 2008 |
Preston North End
|
2–0 |
|
H | ENG · League Cup Round 1 |
| 09 Aug 2008 |
Barnet
|
1–3 |
|
A | ENG · League Two |
| 03 May 2008 |
Chesterfield
|
1–1 |
|
D | ENG · League Two |
| 26 Apr 2008 |
Macclesfield Town
|
1–0 |
|
H | ENG · League Two |
| 19 Apr 2008 |
Chesterfield
|
1–1 |
|
D | ENG · League Two |
| 12 Apr 2008 |
Morecambe
|
1–1 |
|
D | ENG · League Two |
| 05 Apr 2008 |
Chesterfield
|
4–1 |
|
H | ENG · League Two |