Signed from Glasgow Rangers, Alan Hutton won a League Cup winners medal in his first season, but injury hit his second, by which time there had been a change of manager.
An athletic right back, Hutton made his name as an attacking defender in the Rangers side that won the League title and the SFA Cup in 2007-08, but joining Spurs in January of that year for £9 million, he slipped into Juande Ramos' team that won the League Cup before Hutton damaged his foot and required an operation that ruled him out of the latter stages of the season and the start of the next. A recurrence resulted in him missing the bulk of the 2008-09 season and he only came into the side at the tail-end of the campaign, under Harry Redknapp, who had replaced Ramos in October 2008.
A Scotland regular, Hutton developed a bit of a reputation at Spurs, having been pictured being carried out of an Ilford night club drunk following the celebrations after the League Cup win and allegedly fighting outside a pub in Totteridge, North London with his Dad. Rumours circulated about him returning to Scotland with Glasgow Rangers, but at the end of the season, he seemed set to be part of Redknapp's future plans.
Stayed on though and played a few games in the right back slot, before being loaned out to Sunderland and a move to the Black Cats looked on, but during the summer of 2011, he signed for Aston Villa, with Tottenham suffering a considerable loss on his transfer fee.
With a change in management at Villa Park, Hutton fell out of favour with Paul Lambert and went on loan to Nottingham Forest and Real Mallorca.