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