Chesterfield v Middlesbrough, 14 September 1999
| Score | 0-0 |
| Referee | David Pugh |
| Competition | League Cup 2nd round 1st leg |
| Venue | Saltergate, Chesterfield |
| Attendance | 4,941 |
View Chesterfield v Middlesbrough head to head
Starting lineup:
Goalkeeper
Andy Leaning
Defender/Centre back
Steve Blatherwick
Defender/Centre back
Ian Breckin
Defender/Centre back
Steve Woods
Midfielder
Chris Beaumont
Midfielder
Tony Carss
Midfielder
Tom Curtis
Midfielder
Marcus Ebdon
Midfielder
Jamie Hewitt
Forward
David Reeves
Forward
Roger Willis
Substitutions:
| Jamie Lomas for Tom Curtis | 46 |
| Mark Gayle for Andy Leaning | 46 |
Cards:
Starting lineup:
Mark Schwarzer
Goalkeeper
Robbie Stockdale
Defender/Right back
Curtis Fleming
Defender
Gary Pallister
Defender
Colin Cooper
Defender/Centre back
Jason Gavin
Defender/Centre back
Paul Gascoigne
Midfielder
Neil Maddison
Midfielder
Robbie Mustoe
Midfielder
Alun Armstrong
Forward
Hamilton Ricard
Forward
Substitutions:
| Mark Summerbell for Paul Gascoigne | 44 |
Cards:
| Colin Cooper | Y | |
| Gary Pallister | Y |