- 2027-02-08 in 3mo Chesterfield at Gillingham
- 2026-08-31 1mo Gillingham 1 at Chesterfield 1
- 2026-02-17 8mo Gillingham 0 at Chesterfield 1 Sam Curtis ENG-CHEE 90min 1g
- 2025-08-19 1y Chesterfield 1 at Gillingham 4 Armani George Little ENG-GILN 87min 2g
- 2025-04-08 1y Gillingham 1 at Chesterfield 1
- 2024-08-31 2y Chesterfield 0 at Gillingham 1
- 2017-02-15 9y Chesterfield 1 at Gillingham 1
- 2016-09-28 10y Gillingham 3 at Chesterfield 3
- 2016-02-27 10y Chesterfield 2 at Gillingham 1 Lee Novak ENG-CHXD 90min 1g
- 2015-10-10 11y Gillingham 3 at Chesterfield 1 John Egan ENG-GIJT 90min 1g
- 2015-03-18 11y Gillingham 0 at Chesterfield 3 Sam Clucas ENG-CHXD 90min 2g
- 2014-12-20 11y Chesterfield 3 at Gillingham 2 Jimmy Ryan ENG-CHXD 90min 1g
- 2013-02-23 13y Gillingham 1 at Chesterfield 0 Cody McDonald ENG-GIJT 58min 1g
- 2011-05-07 15y Gillingham 1 at Chesterfield 3 Danny Whitaker ENG-CHXD 90min 1g
- 2011-01-26 15y Chesterfield 2 at Gillingham 0 Deane Smalley ENG-CHXD 85min 2g
- 2009-04-18 17y Gillingham 1 at Chesterfield 0 Mark McCammon ENG-GIJT 70min 1g
- 2008-12-06 17y Chesterfield 1 at Gillingham 2 Simeon Alexander Jackson ENG-GIJT 90min 1g
- 2007-04-14 19y Gillingham 1 at Chesterfield 0
- 2006-11-04 19y Chesterfield 1 at Gillingham 2
- 2006-02-04 20y Gillingham 1 at Chesterfield 1
- 1999-02-06 27y Chesterfield 1 at Gillingham 3
- 1998-03-14 28y Chesterfield 0 at Gillingham 1
- 1997-11-04 28y Gillingham 1 at Chesterfield 1
- 1997-04-05 29y Gillingham 2 at Chesterfield 2
- 1996-08-31 30y Chesterfield 1 at Gillingham 0
- 1995-02-11 31y Gillingham 0 at Chesterfield 2
- 1994-11-19 31y Chesterfield 1 at Gillingham 1