Ten Hag’s Heartbreaks vs Pochettino: Man Utd’s Chelsea Loss Draws Comparisons to Ajax’s Spurs Defeat

• Mauricio Pochettino got the better of Erik ten Hag in a Premier League clash on Thursday
• Chelsea came from behind in second-half stoppage time to beat Manchester United 4-3
• The result drew similarities to their previous meeting in 2019 when Spurs defeated Ajax

How much more heartbreak could Mauricio Pochettino bring to Erik ten Hag?

The Dutch manager tasted another painful defeat at the hands of the now-Chelsea boss on Thursday, with Manchester United losing 4-3 in a thrilling encounter at Stamford Bridge.

That result has drawn comparisons to the way ten Hag's Ajax lost to Pochettino's Tottenham Hotspur in the UEFA Champions League semi-finals five years ago.

Sports Brief looks back at that fateful second-leg encounter between the two outstanding managers.

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Ajax's Champions League dream ends in tears

Erik ten Hag and Ajax were feeling good about themselves heading into the second leg of their semi-final showdown with Tottenham in the 2018-19 UEFA Champions League.

The Dutch club won the first leg 1-0 in Spurs' new magnificent stadium, gaining the advantage at the halfway point of the tie.

Donny van de Beek gave Ajax the victory with a strike in the 15th minute, providing them with a priceless away goal heading into the second leg in Amsterdam.

The Eredivisie side looked like they had secured a place in the Champions League final after building a 3-0 lead on aggregate by half-time of the second leg.

Captain, Matthijs de Ligt, gave the home side a dream start, scoring a towering header in the fifth minute. Hakim Ziyech then added another goal in the 35th minute, finding the back of the net off an assist from Dusan Tadic.

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There's no quit with Spurs, though, who staged a miraculous comeback in the second half. They were given a lifeline in the 55th minute when Lucas Moura scored with a composed finish.

The Brazilian pulled another goal back for Spurs just before the hour mark, reducing the deficit on aggregate to 3-2.

Moura's quick-fire double sent Spurs fans inside the stadium into a frenzy, knowing that if they could find another goal, they would advance to the final.

With time winding down in the second half, disaster struck for Ajax. Ten Hag's worst nightmare happened in the sixth minute of added time, with Moura completing his hat-trick with a left-footed shot from 16 yards out, per The Guardian.

The match finished 3-3 on aggregate, with Ajax losing because of the away goals rule. Ten Hag's gut-wrenching loss in the semis saw his best opportunity to win the Champions League title go up in smoke.

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Chelsea edge past Man United in thriller

Pochettino and ten Hag squared off five years later, this time as Premier League managers.

Their reigns at Chelsea and Manchester United haven't gone according to plan, with the two sides outside the top five in the league table ahead of their clash at Stamford Bridge.

United were coming off a disappointing 1-1 draw with Brentford over the weekend, conceding a late goal deep into second-half stoppage time.

That result reportedly didn't sit well with the club's new minority owner, Sir Jim Ratcliffe, putting ten Hag once again on the hot seat.

A victory over Chelsea would ease some of the pressure, but that looked unlikely at the start of the game as the Blues opened up a 2-0 lead inside 20 minutes.

Conor Gallagher opened the scoring with a goal in the fourth minute before Cole Palmer doubled their advantage with a penalty in the 19th minute.

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Man United battled back from that early deficit, scoring three unanswered goals to turn the match around. Alejandro Garnacho and Bruno Fernandes scored goals in the 34th and 39th minutes to tie the match at 2-2.

Garnacho then gave United their first taste of the lead in the 67th minute, heading in Antony's cross past Blues goalkeeper, Djordje Petrovic.

Just when it seemed the Red Devils would leave Stamford Bridge with all three points, Cole Palmer happened. He scored twice deep into second-half stoppage time to turn a 2-3 deficit into a 4-3 win for Chelsea.

Palmer equalised for the Blues with a penalty in the 10th minute of added time. He then crushed United's hearts seconds later, with his deflected effort finding the back of the net.

The defeat proved costly for ten Hag as the Red Devils are now 11 points away from a Champions League spot, per the BBC. With the way things are going, the Dutchman's reign at Old Trafford may soon come to an end.

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Palmer's penalty record for Chelsea

Sports Brief recently reported on Cole Palmer's penalty record this season.

The Chelsea star has scored eight spot kicks for the Blues this campaign.

Palmer is closing in on Yaya Toure's record of 11 penalties without a miss.