- 25 October 2025, Gillingham vs Salford City, 1-2, Lose
- 18 October 2025, Grimsby Town vs Gillingham, 1-0, Lose
- 11 October 2025, Gillingham vs Cheltenham Town, 1-1, Draw
- 04 October 2025, Milton Keynes Dons vs Gillingham, 3-2, Lose
- 27 September 2025, Gillingham vs Harrogate Town AFC, 0-1, Lose
- 25 October 2025, Tranmere Rovers vs Chesterfield FC, 1-1, Draw
- 18 October 2025, Chesterfield FC vs Fleetwood Town, 1-1, Draw
- 11 October 2025, Chesterfield FC vs Salford City, 2-0, Win
- 04 October 2025, Colchester United vs Chesterfield FC, 6-2, Lose
- 27 September 2025, Chesterfield FC vs Newport County, 4-1, Win
Gillingham's dominant performance over Chesterfield FC in their League Two clash was underscored by their clinical finishing and effective defensive play. Despite only managing zero corner kicks compared to Chesterfield's two, Gillingham maximized their attacking opportunities, netting four goals from a limited number of offensive set-piece chances. Their ability to break down Chesterfield's defense early and set the pace with a goal in the 28th minute highlighted their attacking efficiency.
Chesterfield FC struggled to convert possession into goals, managing just one goal shortly after the halftime break. The away side's lack of offensive precision was apparent, with fewer shots on target compared to Gillingham's accuracy in front of goal. Chesterfield's solitary goal came when they momentarily caught the home side off-guard, but they failed to build on this, succumbing to Gillingham's quick counter-attacks and ability to find space behind their lines.
Gillingham's disciplined defensive setup, despite committing 15 fouls, allowed them to maintain control of the match without conceding too many high-risk opportunities. Their defensive resilience was complemented by a well-organized midfield that disrupted Chesterfield's rhythm, and this discipline ensured that Gillingham retained a clean sheet on corner kicks and offsides, showcasing superior tactical awareness and communication among their players.
Despite receiving four yellow cards, Gillingham managed to keep all players on the pitch, while Chesterfield only received one yellow, an indication of both teams’ aggressive approach but differing tenacity and discipline. The match was decided by Gillingham's ability to capitalize on Chesterfield's defensive lapses, precise shooting, and cohesive team play, allowing them to pull away comfortably in the second half with a decisive 4-1 victory.
Form Guide
| Lose | 1-2 | Gillingham vs Salford City | |
| Lose | 1-0 | Grimsby Town vs Gillingham | |
| Draw | 1-1 | Gillingham vs Cheltenham Town | |
| Lose | 3-2 | Milton Keynes Dons vs Gillingham | |
| Lose | 0-1 | Gillingham vs Harrogate Town AFC |
- PLAYED
- 5
- WINS
- 0
- GOALS
- 4:8
- GOALS / MATCH
- 0.8
- Gillingham has lost four matches in a row with a goal difference of 4:8, scoring 0.8 goals average
| Draw | 1-1 | Tranmere Rovers vs Chesterfield FC | |
| Draw | 1-1 | Chesterfield FC vs Fleetwood Town | |
| Win | 2-0 | Chesterfield FC vs Salford City | |
| Lose | 6-2 | Colchester United vs Chesterfield FC | |
| Win | 4-1 | Chesterfield FC vs Newport County |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 10:9
- GOALS / MATCH
- 2
- Chesterfield FC has two wins in its last five matches with a goal difference of 10:9, scoring 2 goals average
Gillingham H2H Chesterfield FC
| Home game | Gillingham | 4 | 1 | Chesterfield FC | Away game | League Two | |
| Away game | Gillingham | 1 | 1 | Chesterfield FC | Home game | League Two | |
| Home game | Gillingham | 1 | 0 | Chesterfield FC | Away game | League Two | |
| Home game | Gillingham | 1 | 1 | Chesterfield FC | Away game | League One | |
| Away game | Gillingham | 3 | 3 | Chesterfield FC | Home game | League One |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 10:6
- GOALS / MATCH
- 2.00
- In the last five matches that these two sides meet, Gillingham overtook Chesterfield FC twice
- Gillingham won twice and had three draw
- Teams played five times head-to-head in the current season with the goals score 10:6; average goals per match – 2.00
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