1999–2000 Scottish Cup
The 1999–2000 Scottish Cup was the 115th staging of Scotland's most prestigious football knockout competition, also known for sponsorship reasons as the Tennent's Scottish Cup. The Cup was won by Rangers who defeated Aberdeen 4–0 in the final.
Semi-finals
----Largest Wins
A list of the largest wins from the competition.| Score | Home Team | Away Team | Stage |
| 0-7 | Queen of the South | Livingston | Third Round |
| 0-7 | Ayr United | Rangers | Semi Final |
| 1-7 | Threave Rovers | Stenhousemuir | First Round |
| 1-5 | Dalbeattie Star | Albion Rovers | Second Round |
| 4-0 | Dundee United | Alloa Athletic | Fourth Round |
| 0-4 | Aberdeen | Rangers | Final |