Middlesbrough v Chelsea, 25 September 1999
| Score | 1-0 to Chelsea |
| Referee | Paul Alcock |
| Competition | Premier League |
| Venue | Riverside Stadium |
| Attendance | 34,183 |
View Middlesbrough v Chelsea head to head
Goals:
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Gianluca Festa
Defender
Curtis Fleming
Defender
Gary Pallister
Defender/Centre back
Colin Cooper
Midfielder
Paul Ince
Midfielder
Juninho
Midfielder
Keith O'Neill
Midfielder
Christian Ziege
Forward
Brian Deane
Forward
Hamilton Ricard
Substitutions:
| Robbie Mustoe for Paul Ince | 35 |
| Paul Gascoigne for Brian Deane | 70 |
| Alun Armstrong for Juninho | 89 |
Cards:
| Keith O'Neill | Y | |
| Hamilton Ricard | Y | |
| Colin Cooper | Y | |
| Christian Ziege | Y | |
| Paul Gascoigne | 90 | R |
1 Chelsea
Goals:
| Bernard Lambourde | 55 |
|
Starting lineup:
Ed de Goey
Goalkeeper
Marcel Desailly
Defender
Graeme Le Saux
Defender
Frank Leboeuf
Defender
Dan Petrescu
Defender
Bernard Lambourde
Defender/Centre back
Chris Sutton
Defender/Forward
Gabriele Ambrosetti
Midfielder
Didier Deschamps
Midfielder
Dennis Wise
Midfielder
Gianfranco Zola
Forward
Substitutions:
| Celestine Babayaro for Gabriele Ambrosetti | 70 |
| Tore André Flo for Gianfranco Zola | 70 |
| Jody Morris for Didier Deschamps | 89 |
Cards:
| Marcel Desailly | Y | |
| Didier Deschamps | Y | |
| Dan Petrescu | Y | |
| Chris Sutton | Y |