Chesterfield 0 Middlesbrough 0
Outcome: Drawn
Date: 9/14/1999
Manager: Bryan Robson
Attendance: 4941
Competition: LeagueCup SecondRound1stLeg
Played at: Saltergate
Goals:
| Goals | Time | Assists |
Team
| Player | Yellow | Red | Subbed |
| Hamilton Ricard | |||
| Alun Armstrong | |||
| Robbie Mustoe | |||
| Paul Gascoigne | |||
| Neil Maddison | |||
| Colin Cooper | |||
| Robbie Stockdale | |||
| Gary Pallister | |||
| Curtis Fleming | |||
| Jason Gavin | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Mark Summerbell |