Chesterfield vs Gillingham predictions, Sep 01, 2026

English League Two, on Tuesday,

Chesterfield

Gillingham

Score, Highlights

Short Preview

As Chesterfield prepares to host Gillingham FC in their upcoming League Two clash on September 1, 2026, both teams are searching for a much-needed victory amid recent struggles. Chesterfield has managed to secure just one win in their last five outings, reflecting a challenging period as they aim to climb the league table. Similarly, Gillingham also finds themselves in a rough patch, securing only one win in their last five matches, which suggests both sides may lack confidence heading into this fixture.

From a tactical perspective, Chesterfield will look to leverage their home advantage, where they typically perform better defensively. Their recent performances indicate a focus on tightening their defensive structure, aiming to capitalize on set pieces and transitional opportunities to find the net. Gillingham, meanwhile, may employ a counter-attacking strategy, utilizing their pace to exploit Chesterfield’s vulnerabilities on the break.

Bookmakers have listed Chesterfield as the favored side at odds of 1.53, with a probability of a home win at 62.5%. The predicted final score of 1:0 suggests a closely contested match that could hinge on a moment of brilliance or a defensive lapse. While Chesterfield holds the edge, the unpredictable nature of football means that all outcomes remain possible.

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 2026-08-29T23:52:03+00:00.

Chesterfield
61.6%
Draw
23.1%
Gillingham
15.3%

Prediction (the most likely score): 1:0

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

Betting Odds

1 X 2
bet_at_home 1.51 4.08 6.20
MarathonBet 1.50 4.05 6.25 Watch Watch and Bet
WilliamHill 1.48 4.00 6.05
Pinnacle 1.55 3.97 5.55
Best for US Customers 1.49 4.00 5.80

Latest Results

29.08.26 Rotherham United – Chesterfield – 2:1
22.08.26 Salford City – Chesterfield – 0:1
15.08.26 Chesterfield – Fleetwood Town – 0:1
08.08.26 Fleetwood Town – Chesterfield – 1:0
31.07.26 Scunthorpe United – Chesterfield – 1:1
29.08.26 Gillingham FC – Northampton Town – 1:1
22.08.26 Fleetwood Town – Gillingham FC – 0:0
15.08.26 Gillingham FC – Walsall FC – 0:3
08.08.26 Gillingham FC – Luton Town – 0:3
31.07.26 Ebbsfleet United – Gillingham FC – 1:2

Facts

  • In the last 5 head-to-head matches, Chesterfield won 1.
  • Chesterfield is currently in poor form (last 5 games: 1 wins).
  • Gillingham has been playing with ups and downs recently (in the last 5 games, wins – 1).
  • Recently, Chesterfield has had a series of away games.
  • In this match, Chesterfield is the undeniable favorite.
  • In the last 12 head-to-head matches, Chesterfield won 4 matches, drew 4 matches, lost 4 matches, and goals 17:18. (average 1.4:1.5).
  • Including home matches between the teams, Chesterfield won 2 matches, drew 2 matches, lost 2 matches, and goals 9:8. (average 1.5:1.3).

    Latest Head To Head

    17.02.26 Chesterfield – Gillingham FC – 1:0
    19.08.25 Gillingham FC – Chesterfield – 4:1
    08.04.25 Chesterfield – Gillingham FC – 1:1
    31.08.24 Gillingham FC – Chesterfield – 1:0
    14.02.17 Gillingham FC – Chesterfield – 1:1

    Standings

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

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