Jamie Carragher believes "football has moved on" from the style of football that brought Jose Mourinho so much success, as he suggested his days as a serial winner may be over.
Speaking to The Herald at a Sky Sports event, Carragher compared the brand of football Mourinho promotes to that of his former Liverpool manager Rafael Benitez, as he argued stifling tactics have been doused by a new brand of high-energy football.
Liverpool manager Jurgen Klopp and Manchester City boss Pep Guardiola have transformed the Premier League landscape since Mourinho led Chelsea to the Premier League title in the 2014/15 season, in comments that are likely to infuriate the fallen champion now in charge of Tottenham.
Mourinho heads into tonight's clash against his former club Manchester United needing a win to revive his side's flagging hopes of Champions League qualification, yet Carragher is not convinced his tactics still have a place at the game's top table.
"I am very wary of saying the game has moved on from managers like Jose Mourinho and Rafael Benitez because they are European Cup winners and top-class coaches, but you question whether they can win with the style of play they use," began Carragher.
"There is no doubt the football we see now, the high-energetic attacking football, is not the football we saw when we won the Champions League under Rafa or when Jose was winning titles with Chelsea. They had a different way.
"I am not one for writing off a style of football or saying this style is right and this style is wrong, but clearly things have changed thanks to managers like Klopp and Guardiola.
"It wasn't that long ago that he won a title with Chelsea in his second spell at the club, but it is just in terms of getting it right and matching the teams that play a different way and are now winning more consistently.
"I like the fact that Mourinho can do a job on a Guardiola team, as he did a few months ago when Spurs beat City 2-0 at home. It adds to the Premier League.
"Sean Dyche plays a bit more direct at Burnley and it's always interesting to see how Liverpool or City fare when they go to Turf Moor and have to play a different style?
"I think it is great that we have different styles and different ways of doing things and I still believe that different styles and different formations can win leagues.
"But things have not started too well for Jose at Spurs and he needs to find a way to get them winning again."
Despite Carragher's pessimism over Mourinho's long-term prospects at Spurs, he believes the Premier League restart will be ready-made for this tactical master to spin a few golden webs and plot a route to short-term success.
The cessation of Premier League football in March was perfectly timed for Mourinho, as he heads into tonight's game against United with Harry Kane and Son Heung-min fully fit after long injury lay-offs.
Yet he believes United have the upper hand in a clash that will have a big impact on the race to secure Champions League football for next season.
"This game will be huge and I think Jose will see this as a great opportunity," says Carragher.
"If Tottenham can come back and they are out of the blocks quicker than anyone, they have a real opportunity to get top four.
"I think they were written off on their chances of that before. He was quoted as saying a few months ago that he couldn't wait for next year to start.
"Having Kane and Son back is massive for them, but I believe they have to win this first game against United to give themselves a chance.
"The pandemic may have come along at the right moment for Spurs as they were in such poor form when we stopped. But it is the flip side for Manchester United - it did not come at a good time at all.
"United may be able to carry on from where they left off but I felt they were almost nailed on for a Champions League position. It goes down to a top-five if Man City's UEFA ban remains in place."
United manager Ole Gunnar Solskjaer will get the chance to pair Bruno Fernandes and Paul Pogba in his midfield for the first time this evening and Carragher believes the duo will be crucial to their hopes of sealing a return to the Champions League.
"Pogba is a quality player, despite the criticism I and many people have directed towards him," he added. "There is always this debate over whether Pogba should play in central midfield or whether he should play behind the No 10.
"With Bruno Fernandes there now, it looks like he will have to play the central midfield role and we have always questioned whether he has the discipline to play that position.
"There is no doubt about Pogba's quality in terms of the passing range from that position, but at times does he have the discipline to play there or at times will he go walking and wandering about to leave his team exposed?
"Maybe he will try and trick on the halfway line and it will be really interesting how Ole sets up his team tactically to get those two players into his team. Pogba and Fernandes are two of United's best players and you have to somehow have to fit them in."