Middlesbrough 2 Chesterfield 1
Outcome: Won
Date: 9/21/1999
Manager: Bryan Robson
Attendance: 25602
Competition: League Cup Second Round 2nd Leg
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Paul Ince | 24 | ||
| Steve Vickers | 87 | ||
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Colin Cooper | |||
| Christian Ziege | |||
| Gary Pallister | |||
| Curtis Fleming | |||
| Jason Gavin | |||
| Robbie Mustoe | |||
| Paul Ince | |||
| Juninho | |||
| Hamilton Ricard | |||
| Alun Armstrong |
Subs
| Player | Yellow | Red | Subbed |
| Robbie Stockdale | |||
| Steve Vickers | |||
| Andy Campbell |