Middlesbrough 2 Arsenal 2
Outcome: Won
Date: 11/30/1999
Manager: Bryan Robson
Attendance: 23157
Competition: League Cup Fourth Round
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Hamilton Ricard | 8 | ||
| Hamilton Ricard | 83 | ||
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Colin Cooper | |||
| Gianluca Festa | |||
| Christian Ziege | |||
| Steve Vickers | |||
| Curtis Fleming | |||
| Paul Ince | |||
| Keith Oneill | |||
| Juninho | |||
| Brian Deane | |||
| Hamilton Ricard |
Subs
| Player | Yellow | Red | Subbed |
| Robbie Mustoe | |||
| Phil Stamp | |||
| Paul Gascoigne |