I turned down Tottenham three or four times – they sent a private jet and I didn't turn up

Ex-Tottenham defender Alan Hutton says he turned the club down "three or four times" while at Rangers - the side Ange Postecoglou's men face in the Europa League at Ibrox this evening (December 12). Hutton eventually did sign for Spurs, but it took a lot of convincing.

The former Scotland international, 40, says Tottenham chartered a private plane to pick him up after agreeing a fee with the 'Gers. But Hutton refused to budge.

"I didn’t want to go," he told The Scottish Sun back in 2022. "I don’t think people know the story, but I actually knocked it back three or four times.

READ MORE: Thomas Frank sets conditions for next job as Ange Postecoglou faces Tottenham challenge

READ MORE: Jamie Carragher has been proven right about Tottenham and Daniel Levy after Cristian Romero rant

"I even remember them sending up a plane and me not turning up for it. Eventually I had a meeting with [Rangers owner] David Murray in Edinburgh and he basically said, 'Look, you need to go'."

It was the mid-way point of the 2007/08 season and Tottenham, under recently-appointed manager Juande Ramos, were looking for someone to compete with Pascal Chimbonda for the right back spot. Hutton said he was flattered by Spurs' interest, and even more impressed by their unwillingness to walk away from the deal in spite of his reluctance to move.

But as a boyhood Rangers supporter he was intent on staying in Glasgow, especially since he'd only just nailed down a starting spot in the first team. "I’d only just got there and then suddenly someone was saying to me, ‘Right, it’s time to leave’," he recalled. "That’s the thing I found most difficult. In fairness to Tottenham, they could easily have walked away.

"At one stage my agent told me they were going to move on to someone else and I told him I was absolutely fine with that. But they came back again and I reluctantly said I’d think about it. I told them I’d go down and speak to them but when the day came I still wasn’t sure, so I just didn’t go to the airport when they had sent a plane up."

Eventually, Hutton agreed to travel to London, and, after meeting Ramos and Spurs chairman Daniel Levy, agreed to sign. He couldn't have asked for a better start to life in north London, with Tottenham lifting the League Cup just weeks into his tenure.

But at the same time, Rangers were flying in the UEFA Cup, and Hutton couldn't help but feel a little left out. "The first six months at Tottenham were great, but I watched Rangers get to the final of the UEFA Cup and it would have been great to have been part of that," he said.

"Leaving after that season would have made me feel better, put it that way. But January transfer windows are manic and I didn’t really have a choice. Tottenham were desperate to sign me but there was a voice in my head saying, 'Do you really want to go there?'"

Hutton was a regular under Ramos, but when the Spaniard was replaced by Harry Redknapp part-way through the following season his fell down the pecking order, and things quickly went south. A loan move to Sunderland followed in the 2009/10 season, and while Hutton was handed plenty of game-time in the 2010/11 - including in the Champions League - he left to join Aston Villa on deadline day in August 2011, having been ousted by an emerging Kyle Walker as the club's first-choice right back.

All in all, Hutton played 66 times for Tottenham, scoring two goals. He retired in 2020, having spent the remainder of his career - save for a season-long loan at Nottingham Forest in 2012/13 - at Villa Park.

Two of his former clubs, Tottenham and Rangers, are set to go head-to-head for just the third time on Thursday evening - with their previous two meetings coming in the UEFA Cup Winners' Cup back in 1962. The teams are neck-and-neck in the Europa League table on 10 points each, though Rangers are a place ahead of Spurs due to their superior goal difference.

Postecoglou's side will be eager to bounce back following their disappointing 4-3 defeat to Chelsea on Sunday. It was their fourth defeat in seven games, and left them 11th in the Premier League table and seven points adrift of the top four.