Middlesbrough v Watford, 13 October 1999
| Score | 1-0 to Middlesbrough |
| Referee | Alan Wiley |
| Competition | League Cup 3rd round |
| Venue | Riverside Stadium |
| Attendance | 8,843 |
View Middlesbrough v Watford head to head
Goals:
| Juninho | 63 |
|
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Curtis Fleming
Defender
Gary Pallister
Defender
Steve Vickers
Defender/Centre back
Colin Cooper
Midfielder
Paul Ince
Midfielder
Juninho
Midfielder
Neil Maddison
Midfielder
Keith O'Neill
Forward
Alun Armstrong
Forward
Brian Deane
Substitutions:
| Hamilton Ricard for Alun Armstrong | 66 |
| Christian Ziege for Keith O'Neill | 76 |
Cards:
| Keith O'Neill | Y | |
| Colin Cooper | Y |
0 Watford
Goals:
Starting lineup:
Alec Chamberlain
Goalkeeper
Nigel Gibbs
Defender
Robert Page
Defender
Paul Robinson
Defender
Steve Palmer
Defender/Centre back
Micah Hyde
Midfielder
Richard Johnson
Midfielder
Peter Kennedy
Midfielder
Charlie Miller
Midfielder
Michel Ngonge
Forward
Nordin Wooter
Forward
Substitutions:
| Tommy Smith for Charlie Miller | 87 |
Cards:
| Nigel Gibbs | Y | |
| Michel Ngonge | Y | |
| Charlie Miller | Y |