Chesterfield 0 Middlesbrough 0
Outcome: Drawn
Date: 9/14/1999
Manager: Bryan Robson
Attendance: 4941
Competition: League Cup Second Round 1st Leg
Goals:
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Colin Cooper | |||
| Curtis Fleming | |||
| Gary Pallister | |||
| Jason Gavin | |||
| Robbie Stockdale | |||
| Neil Maddison | |||
| Paul Gascoigne | |||
| Robbie Mustoe | |||
| Alun Armstrong | |||
| Hamilton Ricard |
Subs
| Player | Yellow | Red | Subbed |
| Mark Summerbell |