Oh My Tip
League Two· Regular Season - 4· Proact Stadium
Chesterfield logoChesterfield
Gillingham logoGillingham

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Chesterfield vs Gillingham Prediction & Betting Tips

Tuesday, 1 September 2026 · Kick-off

No tip was published for this match before kick-off.

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Voting closed at kick-off

Who will win?

Votes: 0
✕ Our model got it wrong

How many goals?

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✓ Our model got it right

Match probabilities

38%Chesterfield
32%Draw
30%Gillingham
Over 2.5 goals23%
Under 2.5 goals77%
Both teams to score31%
Clean sheet either side69%

Bookmaker prices aren't available yet. These figures come from our stats model and will update when markets open.

More Chesterfield vs Gillingham tips

SelectionProbabilityFair oddsBest odds
U3.5Under 3.5 goals91%1.09-
AH1 +1.5Chesterfield +1.5 (Asian Handicap)91%1.10-
AH2 +1.5Gillingham +1.5 (Asian Handicap)87%1.15-
U2.5Under 2.5 goals77%1.30-
1XChesterfield or Draw70%1.44-
BTTS NoBoth teams NOT to score69%1.46-
X2Gillingham or Draw62%1.61-
1Chesterfield to win38%2.65-
XDraw32%3.14-
BTTS YesBoth teams to score31%3.19-
2Gillingham to win30%3.29-
O2.5Over 2.5 goals23%4.35-
AH1 -1.5Chesterfield -1.5 (Asian Handicap)13%7.75-
AH2 -1.5Gillingham -1.5 (Asian Handicap)9%11.28-
O3.5Over 3.5 goals9%11.65-

Chesterfield vs Gillingham preview & analysis

Match preview

Chesterfield host Gillingham in the League Two (Regular Season - 4) at Proact Stadium on Tuesday, 1 September 2026, with kick-off at 18:45 UTC. Here's our full prediction, built from bookmaker prices, current form and head-to-head data.

Head to head

In the last 6 meetings between these sides, Chesterfield have won 1, Gillingham have won 2 and 3 ended level. Those games averaged 2.8 goals, and both teams scored in 4 of them.

What the numbers say

Our model makes Chesterfield narrow favourites: Chesterfield 38%, draw 32%, Gillingham 30%. We expect around 1.6 goals (0.9 - 0.8 in expected goals), with 23% for over 2.5 and 31% for both teams to score.

Head to head

17/02/2026Chesterfield1-0Gillingham
19/08/2025Gillingham4-1Chesterfield
08/04/2025Chesterfield1-1Gillingham
31/08/2024Gillingham1-0Chesterfield
14/02/2017Gillingham1-1Chesterfield
27/09/2016Chesterfield3-3Gillingham

League Two table

#TeamPWDLGDPts
1Salford City logoSalford City10613+519
2Barnet logoBarnet8530+918
3Crewe logoCrewe10460+518
4Gillingham logoGillingham10442+516
5York logoYork9432+615
6Walsall logoWalsall9360+615
7Chesterfield logoChesterfield10433+315
8Cheltenham logoCheltenham10433015
9Bristol Rovers logoBristol Rovers10505-215

Chesterfield vs Gillingham: FAQ

Who is the favourite to win Chesterfield vs Gillingham?

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Chesterfield are favourites. Our model gives Chesterfield a 38% chance of winning, Gillingham 30%, and the draw 32%.

Will both teams score in Chesterfield vs Gillingham?

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We rate both teams to score at 31%, so BTTS No is the better bet.

When does Chesterfield vs Gillingham kick off?

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Chesterfield vs Gillingham kicks off at 18:45 UTC on Tuesday, 1 September 2026 at Proact Stadium, Chesterfield.

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