Rangers, the defending champions, retained their title on 22 April 2000, after their nearest challengers Celtic drew 1–1 with Hibernian.

They replaced Dunfermline Athletic who were relegated after a three-season stint in the top flight, finishing bottom of the league the previous season.

The 1999–2000 Scottish Premier League was won by Rangers for the second successive year, finishing 21 points ahead of nearest rivals Celtic.

[26] It proved to be a brief and unsuccessful reign, however, after being sacked in February 2000, ten points behind Rangers in the league, and in the wake of a Scottish Cup defeat to First Division Inverness Caledonian Thistle.

[27] This was the record for the highest-scoring match in Scottish Premier League history, until Motherwell and Hibernian played out a 6–6 draw in May 2010, also at Fir Park.