During the 1999–2000 Dutch football season, PSV Eindhoven competed in the Eredivisie.
PSV claimed the Eredivisie title with a margin of 16 points between them and second-placed Heerenveen, scoring 105 goals in the process.
Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.
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Johann Vogel - Grasshoppers
Mark van Bommel - Fortuna Sittard
Ivica Kralj - 
Porto
Eric Addo - 
Club Brugge, fl.5.9m Gilles De Bilde - 
Sheffield Wednesday, August| 14 September 1999 | Bayern Munich  | 2–1 | PSV Eindhoven | Olympic Stadium, Munich |
Paulo Sérgio  11', 69' |
Report | Khokhlov 59' |
Attendance: 30,000 Referee: Gilles Veissière (France) |
| 22 September 1999 | PSV Eindhoven | 1–1 |  Valencia | Philips Stadion, Eindhoven |
| van Nistelrooy 72' (pen.) |
Report | Claudio López 4' |
Attendance: 26,500 Referee: Rune Pedersen (Norway) |
| 29 September 1999 | PSV Eindhoven | 0–1 |  Rangers | Philips Stadion, Eindhoven |
| Report | Albertz 85' |
Attendance: 28,000 Referee: Anders Frisk (Sweden |
| 20 October 1999 | Rangers | 4–1 | PSV Eindhoven | Ibrox Stadium, Glasgow |
| Amoruso 18' Mols 39', 80'N. McCann 56' |
Report | van Nistelrooy 45' (pen.) |
Attendance: 50,023 Referee: Pierluigi Collina (Italy) |
| 26 October 1999 | PSV Eindhoven | 2–1 | Bayern Munich | Philips Stadion, Eindhoven |
| van Nistelrooy 39' Nilis 57' |
Report | Santa Cruz 51' |
Attendance: 28,000 Referee: Paul Durkin (England |
| 2 November 1999 | Valencia | 1–0 | PSV Eindhoven | Estadio Mestalla, Valencia |
| Claudio López 70' |
Report | Attendance: 26,266 Referee: Graham Barber (England) |
