- 05 September 2026, Rochdale vs Gillingham, 1-4, Win
- 01 September 2026, Chesterfield FC vs Gillingham, 1-1, Draw
- 29 August 2026, Gillingham vs Northampton Town, 1-1, Draw
- 22 August 2026, Fleetwood Town vs Gillingham, 0-0, Draw
- 15 August 2026, Gillingham vs Walsall, 0-3, Lose
- 05 September 2026, Cheltenham Town vs Grimsby Town, 2-2, Draw
- 01 September 2026, Cheltenham Town vs York City FC, 3-2, Win
- 29 August 2026, Barnet FC vs Cheltenham Town, 2-2, Draw
- 22 August 2026, Swindon Town vs Cheltenham Town, 2-1, Lose
- 15 August 2026, Cheltenham Town vs Rotherham United, 2-1, Win
In an engaging League Two encounter on December 20, 2024, Gillingham and Cheltenham Town shared the spoils in a 2-2 draw, with both teams showcasing periods of dominance. Gillingham struck first in the 24th minute, capitalizing on their early attacking intent with fluid passing and precise finishing. However, Cheltenham's equalizer in the 36th minute came as a result of sustained pressure and intelligent movement, demonstrating their ability to bounce back quickly in the game.
The second half saw Cheltenham take the lead shortly after restart, indicating their persistent efforts and strategic execution on set-pieces. Despite their momentary advantage, Gillingham quickly responded in the 71st minute with a well-coordinated attack that exploited Cheltenham’s defensive lapses. Statistically, Gillingham's five corner kicks to Cheltenham's one highlighted their offensive pressure and territorial advantage throughout the match.
A critical factor influencing the outcome was Cheltenham’s disciplinary issues, evidenced by two yellow cards, which impacted their defensive strategy and fluidity in play. In contrast, Gillingham's clean disciplinary record allowed them to maintain composure and focus. The lack of offsides against Gillingham further illustrated their disciplined and well-organized forward play, contributing to their ability to claw back into the game despite being behind. Overall, the draw reflected a balanced contest influenced by Cheltenham’s caution-inducing fouls and Gillingham’s strategic set-piece advantage.
Form Guide
| Win | 1-4 | Rochdale vs Gillingham | |
| Draw | 1-1 | Chesterfield FC vs Gillingham | |
| Draw | 1-1 | Gillingham vs Northampton Town | |
| Draw | 0-0 | Fleetwood Town vs Gillingham | |
| Lose | 0-3 | Gillingham vs Walsall |
- PLAYED
- 5
- WINS
- 1
- GOALS
- 6:6
- GOALS / MATCH
- 1.2
- Gillingham has won only one out of its last five matches with a goal difference of 6:6, scoring 1.2 goals average
| Draw | 2-2 | Cheltenham Town vs Grimsby Town | |
| Win | 3-2 | Cheltenham Town vs York City FC | |
| Draw | 2-2 | Barnet FC vs Cheltenham Town | |
| Lose | 2-1 | Swindon Town vs Cheltenham Town | |
| Win | 2-1 | Cheltenham Town vs Rotherham United |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 10:9
- GOALS / MATCH
- 2
- Cheltenham Town has two wins in its last five matches with a goal difference of 10:9, scoring 2 goals average
Gillingham H2H Cheltenham Town
| Away game | Gillingham | 1 | 2 | Cheltenham Town | Home game | League Two | |
| Home game | Gillingham | 1 | 1 | Cheltenham Town | Away game | League Two | |
| Away game | Gillingham | 1 | 1 | Cheltenham Town | Home game | League Two | |
| Home game | Gillingham | 2 | 2 | Cheltenham Town | Away game | League Two | |
| Away game | Gillingham | 2 | 2 | Cheltenham Town | Home game | League One |
- PLAYED
- 5
- WINS
- 0
- GOALS
- 7:8
- GOALS / MATCH
- 1.40
- Gillingham lost once in head-to-head matches
- Teams played five times head-to-head in the current season with the goals score 7:8; average goals per match – 1.40
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