Chesterfield 1 Middlesbrough 2
Outcome: Won
Date: 9/21/1999
Manager: Bryan Robson
Attendance: 25602
Competition: LeagueCup SecondRound2ndLeg
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Paul Ince | 24 | ||
| Steve Vickers | 87 | ||
Team
| Player | Yellow | Red | Subbed |
| Juninho | |||
| Hamilton Ricard | |||
| Alun Armstrong | |||
| Robbie Mustoe | |||
| Paul Ince | |||
| Colin Cooper | |||
| Christian Ziege | |||
| Gary Pallister | |||
| Curtis Fleming | |||
| Jason Gavin | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Andy Campbell | |||
| Robbie Stockdale | |||
| Steve Vickers |