Middlesbrough v Chesterfield, 21 September 1999
| Score | 2-1 to Middlesbrough |
| Referee | Bill Burns |
| Competition | League Cup 2nd round 2nd leg |
| Venue | Riverside Stadium |
| Attendance | 25,602 |
View Middlesbrough v Chesterfield head to head
Middlesbrough won 2-1 on aggregate.
Goals:
| Paul Ince | 24 |
|
|
| Steve Vickers | 87 |
|
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Curtis Fleming
Defender
Gary Pallister
Defender/Centre back
Colin Cooper
Defender/Centre back
Jason Gavin
Midfielder
Paul Ince
Midfielder
Juninho
Midfielder
Robbie Mustoe
Midfielder
Christian Ziege
Forward
Alun Armstrong
Forward
Hamilton Ricard
Substitutions:
| Steve Vickers for Gary Pallister | 46 |
| Robbie Stockdale for Jason Gavin | 80 |
| Andy Campbell for Hamilton Ricard | 89 |
Cards:
| Curtis Fleming | Y |
Goals:
| David Reeves | 85 |
|
Starting lineup:
Mark Gayle
Goalkeeper
Michael Simpkins
Defender
Steve Blatherwick
Defender/Centre back
Ian Breckin
Defender/Centre back
Steve Woods
Defender/Centre back
Chris Beaumont
Midfielder
Chris Bettney
Midfielder
Tony Carss
Midfielder
Jamie Hewitt
Midfielder
Jamie Lomas
Midfielder
David Reeves
Forward
Substitutions:
| Jon Howard for Chris Bettney | 63 |
| Paul Holland for Michael Simpkins | 77 |
| Roger Willis for Tony Carss | 77 |
Cards:
| Michael Simpkins | Y |