- Watford 2,
Chesterfield 1Jan 6
- Watford 2,
Chesterfield 1Jan 6
- Chesterfield 1,
Leyton Orient 0Dec 3
- Chesterfield 1,
Leyton Orient 0Dec 3
- Chesterfield 1,
Portsmouth 0Nov 5
- Chesterfield 1,
Portsmouth 0Nov 5
- Horsham 3,
Barnsley 3Nov 3
- First Round DrawOct 15
- West Bromwich Albion 4,
Chesterfield 0Jan 17
- West Bromwich Albion 4,
Chesterfield 0Jan 17
- Accrington 1,
Boreham Wood 1Jan 7
- West Bromwich Albion 3,
Chesterfield 3Jan 7
- West Bromwich Albion 3,
Chesterfield 3Jan 7
- Brighton 5,
Middlesbrough 1Jan 7
- The Emirates FA Cup Meets Sustainable Fashion Chesterfield & Boreham WoodJan 5
- Gillingham 1,
Dagenham 1Nov 26
- Chesterfield 2,
AFC Wimbledon 0Nov 26
- Chesterfield 2,
AFC Wimbledon 0Nov 26
- Chislett Brace Sends The Dons Into The Second Round | Wimbledon 3-1 WeymouthNov 16
- Salford City 0,
Peterborough United 0Nov 5
- Chesterfield 1,
Northampton 0Nov 5
- Chesterfield 1,
Northampton 0Nov 5
- First Round DrawOct 17
- Chelsea's Road to Wembley | All Goals & HighlightsApr 12
- FULL MATCH | Chelsea v Chesterfield | Emirates FA Cup Third Round 2021-22Jan 29
- Lukaku on Target to Send The Blues Through! | Chelsea 5-1 ChesterfieldJan 9
- Chelsea v Chesterfield | Key Moments | Third RoundJan 8
- Third Round DrawDec 6
- Mandeville & Kellerman Knock Out Salford | Salford City 0-2 ChesterfieldDec 6
- Salford City v Chesterfield | Key Moments | Second RoundDec 5
- Second Round DrawNov 8
- Ten Man Chesterfield Make Second Round | Chesterfield 3-1 Southend UnitedNov 7
- First Round DrawOct 17
- Emirates FA Cup First Round DrawOct 15
- Emirates FA Cup First Round DrawOct 26
- Grimsby Town 2,
Chesterfield 0Dec 2
- Billericay 1,
Chesterfield 1Nov 10
- Billericay 1,
Chesterfield 1Nov 10