When history looks back on the Mauricio Pochettino era at Tottenham, and specifically on the last three seasons, how will it judge them?

Saturday’s FA Cup semifinal against Manchester United at Wembley could go a long way toward answering that question. Because Saturday’s FA Cup semifinal against Manchester United was one of opportunities squandered. And that, fairly or unfairly, could end up defining the past three years of Tottenham Hotspur football.

They have, by many measures, been the best three-year stretch in the club’s history. On aggregate, in the Premier League, they’ve been bettered only by Manchester City – and really only by City’s 2017-18 campaign. Tottenham’s 224 points over less than three seasons are more than Manchester United’s tally in that time; more than Liverpool’s; more than Chelsea’s; more than Arsenal’s.

And yet there’s a dichotomous stat that was confirmed Saturday at Wembley. A frustrating stat. The best three-year run in Tottenham history has capped off what is now the longest Tottenham trophy drought since World War II.

United’s come-from-behind 2-1 victory ensured Spurs would go an entire decade without lifting silverware, an unjust symbol of what has otherwise been the most promising and successful spell for Tottenham since the formation of the Premier League.

On the other hand, it ensured United would have one last shot at a trophy in 2017-18.

Jose Mourinho, in contrast to Pochettino and Spurs, has only once completed a full season without a trophy since arriving at FC Porto in 2002. His career, and his teams, have been defined by ruthlessness in big games. And that was the story of Saturday.

Tottenham took an early lead through Christian Eriksen and Dele Alli. The former drilled a bounding cross through the six-yard box, and the latter met it with a wonderful lunging finish at the far post:

Over the first quarter of the match, Spurs had several chances to double their lead. They struck woodwork. They missed chances.

And United, as Mourinho teams seemingly always do, made them pay.

Paul Pogba bullied Mousa Dembele off the ball in his own defensive third midway through the first half, and set up Alexis Sanchez for the equalizer:

In the second half, Spurs were still in control. But Ander Herrera, as true to his box-to-box midfield role as could be, gave United the lead. He finished off a back-to-front, side-to-side counter at one end moments after killing off a Tottenham attack with a header to David De Gea at the other.

United, as clinical as ever, was on top. Despite constant Tottenham pressure, it stayed there. And it will be favored going into the final. Favored to salvage one trophy from Mourinho’s second season in charge after two from the first.

Tottenham, meanwhile, would just love one trophy. Any trophy. Any time. Between World War II and the present day, it has won 16, never with more than 10 season in between honors. But has been shut out since a 2008 League Cup triumph.

The club has been reveling in a golden age, competing with England’s best on the back of young stars despite significantly less spending. It has been better than United, the richest club in the world, three years in a row now.

But somehow, it has nothing to show for it. Every opportunity has become a near-miss. Spurs have lost four FA Cup semifinals and two League Cup finals. They coughed up a Premier League title that could have been theirs to Leicester. This season, they took down Real Madrid in the Champions League group stage, seemingly announcing their arrival as a force in Europe, only to naively throw away a round of 16 tie to Juventus.

There is no one problem. No single flaw or failure that explains the trend. Nothing Pochettino or Spurs must overhaul to end it. Sustain the current level of production, and the rewards will come.

But they haven’t yet. Such is football. And when football is as cruel as it has been to Tottenham over the past decade, not even young talent, sound management and impressive performances can offer sufficient consolation.

– – – – – – –

Henry Bushnell covers global soccer, and occasionally other ball games, for Yahoo Sports. Have a tip? Question? Comment? Email him at henrydbushnell@gmail.com or follow him on Twitter @HenryBushnell.

More soccer from Yahoo Sports:
• Bushnell: The evolution that will define post-Wenger Arsenal
• 13 possible successors for Arsene Wenger at Arsenal
• Gulino: Wenger’s legacy is now up to us to figure out
• 9 things to know about the Champions League semifinal matchups
• A fan’s oral history of the USMNT’s nightmare in Trinidad