Rangers v PSV Eindhoven, 20 October 1999
| Score | 4-1 to Rangers |
| Referee | Pierluigi Collina |
| Competition | UEFA Champions League Group F |
| Venue | Ibrox Stadium, Glasgow |
| Attendance | 50,083 |
4 Rangers
Goals:
| Lorenzo Amoruso | 18 |
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| Michael Mols | 38 |
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| Neil McCann | 55 |
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| Michael Mols | 79 |
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Starting lineup:
Goalkeeper
Stefan Klos
Defender
Craig Moore
Defender
Tony Vidmar
Defender/Centre back
Lorenzo Amoruso
Full back
Sergio Porrini
Midfielder
Barry Ferguson
Midfielder
Derek McInnes
Midfielder
Giovanni van Bronckhorst
Forward
Neil McCann
Forward
Michael Mols
Forward
Rodney Wallace
Substitutions:
| Jorg Albertz for Neil McCann | 70 |
| Jonatan Johansson for Michael Mols | 80 |
| Andrei Kanchelskis for Rodney Wallace | 87 |
Cards:
1 PSV Eindhoven
Goals:
| Ruud Van Nistelrooy | penalty | 45 |
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Starting lineup:
Ivica Kralj
Goalkeeper
Jan Heintze
Defender
Youri Nikiforov
Defender
Rob Wielaert
Defender
Ernest Faber
Centre back
Dmitri Khokhlov
Midfielder
Ovidiu Stîngă
Midfielder
Mark van Bommel
Midfielder
Johann Vogel
Midfielder
Luc Nilis
Forward
Ruud Van Nistelrooy
Forward
Substitutions:
| Joonas Kolkka for Rob Wielaert | 30 |
| Dennis Rommedahl for Ovidiu Stîngă | 73 |
| Arnold Bruggink for Luc Nilis | 85 |
Cards:
| Mark van Bommel | Y |