Prior the beginning of the season 2005-06, the club launched the controversial 'Young Guns' initiative. The players, manager Peter Jackson, assistant manager Terry Yorath, and coach Martyn Booty posed for the 2006 schedule in cowboy outfits.[4] Six of the younger players featured on the cover of the corporate hospitality brochure.

Despite suffering defeat to Nottingham Forest on the first day of the season, Huddersfield started the 2005-06 season brightly and were top of the table by mid-October. During the season they got the opportunity to show their pedigree by playing at Blackburn Rovers in the Carling Cup, which they lost 3-1.

Then they had a big money-spinning FA Cup tie at Chelsea in January. They showed superb fight to only lose 2-1, but many predicted it could be the turning point in Town's season, as they hadn't won a match since being drawn against them, a month earlier.

With the season heading towards the end, Town had to prepare for the play-offs after a poor April, which watched them lose out on automatic promotion to the Championship. The goals of Pawel Abbott, Gary Taylor-Fletcher, Andy Booth, Danny Schofield and Sheffield Wednesday loan signing David Graham guided Huddersfield to have the joint-second best scoring record in the division behind Swansea City.

Huddersfield defeated Barnsley 1-0 at Barnsley in the playoff semi-final first leg but lost 1-3 (2-3 on aggregate) in the return.