Cheltenham Town vs Chesterfield predictions, Sep 26, 2026

Score, Highlights

Short Preview

As Cheltenham Town prepares to host Chesterfield on September 26, 2026, the matchup promises to be competitive, reflecting the teams’ recent form. Cheltenham, with 2 wins in their last 5 matches, has shown flashes of resilience but will be keen to improve their consistency at home, particularly against a side looking to capitalize on their current momentum.

Chesterfield enters this fixture in better shape, having secured 3 victories in their last 5 games. This confidence may serve as a tactical advantage as they aim to exert early pressure on the Cheltenham defense.

Bookmakers have set the odds at 2.94 for a Cheltenham win, reflecting their status as underdogs, while an away win for Chesterfield is favored at 2.18. Predictions suggest a 31% chance of a home victory, a 25.2% possibility of a draw, and an encouraging 43.4% likelihood of an away win for Chesterfield.

Ultimately, the contest will hinge on Cheltenham’s ability to capitalize on home advantage and contain Chesterfield’s potent attacking threat. Both teams will be looking to seize critical points in this tightly contested League Two clash. As with any match, the outcomes remain uncertain, making for an interesting encounter.

This preview is generated with the Welcome.Bet AI Insights Engine, combining form data, betting odds, and semantic SEO optimization to deliver relevant match analysis for fans and bettors alike from 2026-09-20T00:52:02+00:00.

Cheltenham 31.4%

Draw 25%

Chesterfield 43.6%

Prediction (the most likely score): 1:1

Outrights of English League Two Chesterfield: 6.57% Cheltenham: 1.63%

Watch and Bet Cheltenham – Chesterfield available at: Bet Now (Full Screen)

Betting Odds

	1	X	2
	2.94	3.91	2.15
	2.94	3.7	2.13	Watch and Bet
	2.85	3.8	2.1
	2.93	3.61	2.18
	2.95	3.6	2.07

Latest Results

19.09.26 Colchester United – Cheltenham Town – 1:1 12.09.26 Crawley Town – Cheltenham Town – 1:3 05.09.26 Cheltenham Town – Grimsby Town – 2:2 01.09.26 Cheltenham Town – York City – 3:2 29.08.26 Barnet – Cheltenham Town – 2:2

19.09.26 Chesterfield – York City – 2:0 15.09.26 Chesterfield – Manchester City U21 – 5:3 12.09.26 Oldham Athletic – Chesterfield – 1:2 05.09.26 Chesterfield – Barnet – 3:3 01.09.26 Chesterfield – Gillingham FC – 1:1

Facts

One of the standout fixtures of the round, featuring two top-tier sides (ranked 5th in the Promotion ~ League Two PlayoffsSemi~finals) and 8th).

In the last 5 head-to-head matches, Cheltenham won 1.

Both teams are currently displaying solid and consistent form.

Cheltenham could enjoy a physical edge thanks to more rest days ahead of this match.

Recently, Chesterfield has enjoyed a sequence of home fixtures.

Chesterfield is expected to hold a slight competitive edge in this match.

In the last 10 head-to-head meetings, Cheltenham has recorded 3 wins, 2 draws, and 5 losses, with a goal aggregate of 8:15 (averaging 0.8:1.5 goals per game).

Specifically in home fixtures for Cheltenham against this opponent, the record stands at 2 wins, 1 draw, and 2 losses, with 4:7 goals (averaging 0.8:1.4 per game).

Latest Head To Head

03.04.26 Chesterfield – Cheltenham Town – 1:0 09.08.25 Cheltenham Town – Chesterfield – 0:2 01.02.25 Cheltenham Town – Chesterfield – 1:0 21.09.24 Chesterfield – Cheltenham Town – 1:1 17.03.18 Cheltenham Town – Chesterfield – 1:1

Standings

		Pl	W	D	L		Diff	Pts
1	Barnet	7	4	3	0	17:10	7	15
2	Walsall	7	3	4	0	10:4	6	13
3	Grimsby	7	3	4	0	11:6	5	13
4	Gillingham	7	3	3	1	11:6	5	12
5	Cheltenham	7	3	3	1	14:11	3	12
6	Bristol Rovers	7	4	0	3	12:11	1	12
7	York City	7	3	2	2	13:10	3	11
8	Chesterfield	7	3	2	2	10:8	2	11
9	Crewe	7	2	5	0	7:5	2	11
10	Tranmere	7	2	4	1	9:7	2	10
11	Fleetwood	7	2	4	1	8:7	1	10
12	Salford	7	3	1	3	8:9	-1	10
13	Swindon	7	3	1	3	8:11	-3	10
14	Rotherham	7	2	3	2	10:10	0	9
15	Colchester	7	2	3	2	8:10	-2	9
16	Oldham	7	2	1	4	8:9	-1	7
17	Rochdale	7	2	1	4	7:10	-3	7
18	Shrewsbury	7	2	1	4	5:11	-6	7
19	Newport	7	1	3	3	10:11	-1	6
20	Exeter	7	1	3	3	4:5	-1	6
21	Accrington	7	1	3	3	10:13	-3	6
22	Northampton	7	1	3	3	3:6	-3	6
23	Port Vale	7	1	2	4	3:9	-6	5
24	Crawley	7	1	1	5	6:13	-7	4

English League Two Outrights

1. Barnet: 5.33 (15.37%)

2. Bristol Rovers: 6.9 (11.87%)

3. Salford: 7.28 (11.25%)

4. York City: 7.57 (10.82%)

5. Grimsby: 9.07 (9.03%)

6. Chesterfield: 12.47 (6.57%)

7. Walsall: 17.17 (4.77%)

8. Oldham: 23 (3.56%)

9. Crewe: 25.83 (3.17%)

10. Colchester: 26.33 (3.11%)

11. Port Vale: 29.17 (2.81%)

12. Rotherham: 42.17 (1.94%)

13. Fleetwood Town: 42.17 (1.94%)

14. Gillingham: 42.17 (1.94%)

15. Tranmere: 43 (1.9%)

16. Swindon: 43 (1.9%)

17. Cheltenham: 50.17 (1.63%)

18. Northampton: 65.33 (1.25%)

19. Exeter: 66.17 (1.24%)

20. Rochdale: 66.17 (1.24%)

21. Shrewsbury: 100.17 (0.82%)

22. Accrington: 116.83 (0.7%)

23. Crawley Town: 133.5 (0.61%)

24. Newport: 150.17 (0.55%)

Cheltenham Town – Chesterfield and other English League Two events on our partner.