It was competed for by the 30 member clubs of the Scottish Football League.
The defending champions were Falkirk, who defeated Queen of the South 1–0 in the 1997 final.
[1] The final was played on 21 November 1999,[2] between Inverness Caledonian Thistle and Alloa Athletic at Excelsior Stadium in Airdrie.
Forfar Athletic and Livingston received random byes into the second round.
^ The 1998–99 tournament was suspended due to lack of sponsorship