1999–2000 Rangers F.C. season Scottish Cup Scottish Cup

| Date_ | Round | Opponent | Venue | Result_ | Attendance | Scorers |
|---|---|---|---|---|---|---|
| 30 January 2000 | R3 | St. Johnstone | A | 2–0 | 9099 | Numan , Van Bronckhorst |
| 19 February 2000 | R4 | Greenock Morton | A | 1–0 | 8600 | Moore |
| 12 March 2000 | QF | Hearts | H | 4–1 | 31864 | Ferguson , Numan , Amoruso , Dodds ( pen. ) |
| 8 April 2000 | SF | Ayr United | N | 7–0 | 38357 | Rozental (2), Kanchelskis , Wallace , Dodds (3) |
| 27 May 2000 | F | Aberdeen | N | 4–0 | 50865 | Van Bronckhorst , Vidmar , Dodds , Albertz |