Spurs - third in the Premier League standings - have not claimed silverware since hoisting the EFL Cup trophy aloft in 2008, while they last won the FA Cup in 1991. How they respond to that challenge represents something of a referendum on his management.
Jose Mourinho's men tightened their grip on the Premier League runners-up spot this week but a title battle with champions Manchester City never materialised and they limped out of the Champions League in the first knockout stage. Not concerned about the fineries of how his teams plays, he has, more often than not, been able to guarantee trophies at the clubs he has managed and it hasn't been a different story at Old Trafford.
"That was an idea here - that to attract top players, Tottenham need to play in the Champions League", he added.
But when it comes to winning pots, Tottenham are perhaps the biggest underachievers in English football. "But if you are going to change the vision or put the club in a different level, you must compete for and then win the Premier League and Champions League".
Victory in those four games alone would see United just two points behind City in the race for the title.
"It will mean more to Pochettino, being his first experience to win something, and he has far more variety and better technical players, who he's improved and advanced as a team".
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He said: "That is what we are changing at Tottenham". Instead, Manchester City have had a record-breaking season where they have truly proven themselves to be worthy champions.
Starting with the Red Devils, United have failed to meet expectations this season.
Everton boss Sam Allardyce jokingly awarded himself a rating of 11 out of 10 after Toffees fans were sent a survey asking how they felt the former England manager was managing at Goodison Park. But West Brom have done a number on them.
The other semifinal Sunday pits Antonio Conte's Chelsea against relegation-threatened Southampton. Or is the decline real and more deep set?
"We gave no chance to the opponents, which is what Manchester City did".
Here, Press Association Sport takes a look at the main talking points heading into the weekend.
Two of the Premier League's most impressive forwards face-off at Wembley this weekend, each hoping to fire their side to the FA Cup final. We feel that familiarity with Wembley could play into Spurs' hands, and we are backing them for a win.