Middlesbrough 1 Watford 0
Outcome: Won
Date: 10/13/1999
Manager: Bryan Robson
Attendance: 8843
Competition: League Cup Third Round
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Juninho | 63 | ||
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Colin Cooper | |||
| Gary Pallister | |||
| Steve Vickers | |||
| Curtis Fleming | |||
| Paul Ince | |||
| Neil Maddison | |||
| Keith Oneill | |||
| Juninho | |||
| Brian Deane | |||
| Alun Armstrong |
Subs
| Player | Yellow | Red | Subbed |
| Christian Ziege | |||
| Hamilton Ricard |