Sky Sports pundit Gary Neville has compared Leeds United under David O’Leary to Tottenham Hotspur under Mauricio Pochettino, going on to described the Whites as a “big club” and playing at Elland Road as “unbelievable”.
Leeds promoted O’Leary to the role of manager in October 1998 and the Whites finished fourth in the Premier League that season before claiming a third-placed finish and a Champions League spot in 1999-2000.
The Elland Road side maintained their elite form during the 2000-01 season, culminating in a fourth-placed Premier League finish and a memorable run to the Champions League semi-finals.
Despite that successful period, Leeds failed to win a major honour as they were unable to turn impressive results and performances into trophies, and though they finished finished fifth in 2002, they went on to be relegated two years later amid mounting financial problems.
Tottenham, meanwhile, enjoyed a bright period under Pochettino which featured Premier League title challengers and a run to the 2018-19 Champions League final, but that too didn’t yield any silverware.
“I think Tottenham are the modern equivalent of that Leeds team,” Manchester United legend Neville told Sky Sports. “Tottenham haven’t gone onto do what they should have done – maybe they should have won the league the year Leicester won it and could have won a Champions League with a little more luck.
“This Tottenham team is now coming to an end or has come to an end. Teams like Leeds caught you up but never went on to do it. There was something missing. Clubs like Arsenal, Liverpool and Manchester United have had history to build on to win trophies, there’s a mentality within the club to win trophies. Leeds were trying to build that mentality during that period.
“You always felt Leeds were getting nearer and nearer – like Tottenham were getting nearer and nearer. And then you think, how are they going to get back? Leeds has always felt like a huge club. When I get asked what is a big club I always think of Leeds United. The feeling when you go and play football there is unbelievable – it’s different.”
While the overall sense of underachievement is similar in that Leeds side under O’Leary and the Spurs team under Pochettino, there were several notable differences.
One team ended up spending beyond its means, ultimately underachieved and, given the directors had budgeted for Champions League qualification – which didn’t come – it proved disastrous.
Spurs, meanwhile, had come within a whisker of silverware but under-investment in the squad, if anything, has been responsible for their woes this season.