The 2006 format was a single match between the two Dundee clubs, although the inaugural competition (2005) was a standard four-team knock-out competition.
The Cup's inaugural showing was a standard four-team cup format, which saw Dundee United beat Sheffield Wednesday 2–1 in the final.
United beat rivals Dundee in the first semi-final, while Sheffield Wednesday saw off Wolverhampton Wanderers on penalties in the other.
[1] On 22 June 2006, sponsorship was announced for the competition, which would see it renamed the Evening Telegraph Challenge Cup; Radio Tay would also sponsor the event.
In 2007, the tournament was to be scheduled for an international weekend during the season, as Dundee United played Barcelona and did not wish to play a pre-season derby so close after that match.