The 1999–2000 season was the 91st year of football played by Dundee United, and covers the period from 1 July 1999 to 30 June 2000.
United sold top scorer Billy Dodds to Rangers at the start of December and immediately the club's fortunes changed.
The same team knocked United out of the CIS Insurance Cup, this time at the semi-final stage.
Despite leaving the club in early December and playing only eighteen matches, Billy Dodds was the top goalscorer, scoring ten goals.
Seven players left the club during the season with only one transfer – Billy Dodds to Rangers – bringing in a fee (£1.3m).