Ruben Amorim is set for his first Premier League meeting with Tottenham, but the Portuguese could easily have found himself in the opposite dugout.
Manchester United boss Amorim came up short against Spurs in the Carabao Cup quarter-finals, and has found things tough in his three months at Old Trafford. Ange Postecoglou's side are chasing a third win this season against the Old Trafford club, having sealed a 3-0 win over an Erik ten Hag-managed United in the autumn, and victory would ease the pressure on the Londoners' under-fire boss.
Ten Hag was sacked by United a few weeks later, with Amorim taking over in November. The former Sporting boss turned down a move to West Ham earlier in the year, describing talks with the club as a mistake, but was prepared to trade Lisbon for Manchester midway through the season.
Before those talks, however, Tottenham explored a move for Amorim. They ended up with Postecoglou instead, though, and it was reported at the time that Daniel Levy was part of the reason why.
In March 2023, Spurs had just sacked manager Antonio Conte after a very vocal outburst against the club Cristian Stellini was the initial interim replacement, but A Bola (via Sport Witness) suggested Amorim was being eyed as a potential longer-term successor.
At the time, Sporting were playing catch-up in the race for Champions League football. They would ultimately end the campaign with 36 points from their final 14 games, but it was only enough for fourth place.
Amorim's Sporting impressed against Spurs in the Champions League, and knocked Arsenal out of Europe after dropping down to the Europa League. The Portuguese was on Spurs' shortlist as a result, but A Bola indicated at the time that there were a few obstacles to a move.
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One of these, the paper claimed, was chairman Levy's "tempestuous temper". Conte was the third manager dismissed by Levy in the four years since long-serving boss Mauricio Pochettino left North London, with Jose Mourinho and Nuno Espirito Santo both coming and going in short order.
A Bola also cited Amorim's reluctance to leave mid-season, along with his desire to win a second league title before leaving Sporting. Perhaps it was because of that 2023-24 title that he was more open to a mid-season move to Old Trafford a few months later.
Spurs sat fourth when Conte made way, but ended the season in eighth after a nightmare spell under Stellini forced them to replace the interim with another interim. They rebounded with a fifth place finish last term but have struggled to deal with an injury crisis this time around.
United finished eighth last year, but they and Spurs are now both firmly ensconced in the bottom half of the table. Both will remain there come 6.30 on Sunday evening, but it remains a chance for both managers to make the argument that they - and their respective clubs - got the right man.