Things ended on a sour note for at - after even the serial-winning Portuguese coach failed to bring a trophy back to north London. Rightly or wrongly, he was sacked by a few days out from HIS golden opportunity to win silverware for the Lilywhites.
That was in 2021, of course, and quite a lot has changed since then. But one ambition remains the same.
Tottenham are potentially 180 minutes away from getting their hands on the crown. , while Manchester United could wait in the showpiece as they too hold the initiative over Athletic Club in the other last-four clash.
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Mourinho, now at Fenerbahce after a spell with Roma post-Tottenham, needs no introduction to either.
heading towards kick-off. But while Man Utd can rely on home comforts tonight, 's team can do anything but as they prepare to lace up their boots - perhaps moulds at that - in the Arctic Circle.
Colder than home, naturally, there's also the small matter of an artificial surface to contend with at the Aspmyra Stadion. Many have tried and failed to conquer those conditions, not least Mourinho's Roma.
Indeed, the Italian outfit - with Mourinho at the helm - were beaten not once but twice at the same venue in the 2021/2022 season. Despite those defeats, a 6-1 verdict in Group C before a quarter-final reunion resulted in a much more respectable 2-1 reverse, Roma went on to win the Conference League that season!
Not too much damage done, then, but the former Spurs and Chelsea manager did not hold back when discussing Bodo/Glimt's artificial surface - blaming it for an injury picked up by Gianluca Mancini at the time.
"To be honest, the thing that worries me the most is the injury for Mancini," said Mourinho.
"It's a concern, it's something caused by playing on a plastic turf."
All's well that end's well. Roma overcame their 2-1 quarter-final deficit to not only make the last-four, but go on to reach the 2022 showpiece and triumph in that, as well. Fast forward to the present, as Tottenham gear up to make the best of what they can in challenging surroundings, Mourinho's thoughts on artificial surfaces are clear.
Last season, the 62-year-old and his Fenerbahce side locked horns with Swiss side Lugano - while even a dramatic 4-3 win was not enough to heighten Mourinho's opinion.
"High level football in [a] plastic pitch is not high level football," he said.
"The ball is slow and the players can't dribble, they run with the ball and the ball stays behind. The game is slow, so honestly I don't understand why UEFA allows Champions League in [a] plastic pitch."
Should they get through tonight unscathed - in terms of rubber-stamping their progression to the Europa League final and in the treatment room - then Postecoglou might not necessarily hate the artificial surface as much as one of his north London predecessors.
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