Steffen Freund has been stunned by Leeds' decline since his playing days, but the Tottenham assistant manager has warned his squad they cannot afford to underestimate the npower Championship side on Sunday.
Spurs head to Elland Road this weekend looking to book their place in the last 16 of the FA Cup.
Freund, who played for Spurs from 1998 to 2003, only tasted victory over Leeds once in the league during his time at the London club.
During that time Leeds enjoyed one of their most successful periods in recent history, challenging for the Barclays Premier League and reaching the semi-finals of the Champions League, where they lost to Valencia in 2001.
Since Freund left Spurs, Leeds have been on the decline. Over-expenditure on transfer fees and wages meant the club had to sell their best players and they now sit 11th in the Championship having previously spent three years in English football's third tier.
"Yes of course I'm surprised," said Freund, who also played against Leeds for Spurs in the FA Cup 14 years ago.
"During my time here as a player we always had difficult games at Elland Road."
"They were a really strong team, they finished in the semi-finals of the Champions League and they are not in the Premier League at the moment.
"That's why it's a surprise for me, but still they have a very strong squad. They beat Southampton and Everton in the League Cup this season.
"They've got nine wins and three defeats at home. It will be a difficult game for us."
Although Spurs are on an eight-match unbeaten run, Andre Villas-Boas' men are still far from assured of a top four finish this term.
Spurs are just three points ahead of fifth-placed Everton and they also have the inconvenience of two potentially tricky games against Norwich and West Brom in the coming week.
Given how much the competition means to Spurs, it seems unlikely they will rest a large chunk of their first team, however.
"We take it seriously," the German said.
"The FA Cup is one of the biggest cups in the world and we do that for every game.
"The FA Cup is massive for Tottenham Hotspur. We've won it eight times and we'd like to do it again."
Tottenham have been relatively quiet in the transfer window so far, securing the Bosman signing of Lewis Holtby and the capture of 20-year-old defender Zeki Fryers from Standard Liege.
Spurs have become renowned for their late forays in to the transfer market, however, and they have already tried - and failed - with two bids to bring Holtby in this month, rather than at the end of the season.
Freund was keeping his cards close to his chest on Tottenham's pursuit of the Schalke midfielder today.
"At the moment he will be here in the summer," Freund said.
"I can't give you an update, I'm not involved in negotiations about new players."
William Gallas and Jan Vertonghen are expected to travel to Leeds after overcoming their respective groin and illness problems, but Spurs remain without striker Emmanuel Adebayor, who is away at the African Nations Cup.