Macclesfield Town 1 Middlesbrough 2
Outcome: Won
Date: 9/19/2000
Manager: Bryan Robson
Attendance: 5144
Competition: LeagueCup SecondRound1stLeg
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Noel Whelan | 87 | ||
| Mark Summerbell | 90 | ||
Team
| Player | Yellow | Red | Subbed |
| Noel Whelan | |||
| Hamilton Ricard | |||
| Alun Armstrong | |||
| Paul Ince | |||
| Mark Summerbell | |||
| Stuart Parnaby | |||
| Colin Cooper | |||
| Dean Gordon | |||
| Gianluca Festa | |||
| Jason Gavin | |||
| Chris Bennion |
Subs
| Player | Yellow | Red | Subbed |
| Joseph Desire-Job | |||
| Alen Boksic | |||
| Keith Oneill |