AC Milan v Chelsea, 26 October 1999
| Score | 1-1 |
| Referee | Nikolai Levnikov |
| Competition | UEFA Champions League Group H |
| Venue | Stadio Giuseppe Meazza, Milan |
| Attendance | 74,855 |
View Chelsea v AC Milan head to head
1 AC Milan
Goals:
| Oliver Bierhoff | 74 |
|
Starting lineup:
Goalkeeper
Christian Abbiati
Defender
Alessandro Costacurta
Defender
Paolo Maldini
Defender
Claudio Serginho
Defender/Centre back
Roberto Ayala
Midfielder
Massimo Ambrosini
Midfielder
Gennaro Gattuso
Midfielder
Andres Guglielminpietro
Midfielder
Leonardo
Forward
Oliver Bierhoff
Forward
Andriy Shevchenko
Substitutions:
| Zvonimir Boban for Leonardo | 57 |
| Pierluigi Orlandini for Claudio Serginho | 86 |
Cards:
| Leonardo | Y | |
| Alessandro Costacurta | Y | |
| Roberto Ayala | Y | |
| Massimo Ambrosini | Y |
1 Chelsea
Goals:
| Dennis Wise | 77 |
|
Starting lineup:
Ed de Goey
Goalkeeper
Albert Ferrer
Defender
Marcel Desailly
Defender
Frank Leboeuf
Defender
Dan Petrescu
Defender
Celestine Babayaro
Defender/Left back
Didier Deschamps
Midfielder
Gus Poyet
Midfielder
Dennis Wise
Midfielder
Tore André Flo
Forward
Gianfranco Zola
Forward
Substitutions:
| Jody Morris for Dan Petrescu | 46 |
| Roberto Di Matteo for Gus Poyet | 75 |
| Gabriele Ambrosetti for Gianfranco Zola | 81 |
Cards:
| Gianfranco Zola | Y | |
| Albert Ferrer | Y |