Man Utd left with £84m transfer regret after two-time van Gaal failure

Manchester United have been given another untimely reminder of what could have been after Bayern Munich star Thomas Muller penned a new contract extension at the Allianz Arena on Tuesday.

Muller is one of the most decorated footballers in history and might well have been continuing that winning run with United had Louis van Gaal twice got his wish of signing the forward.

The 32-year-old has won the most trophies of any other German international in the history of the game having surpassed Bastian Schweinsteiger 's record of 26. Now, with the Bayern man having committed his future to the Bavarian giants with a new deal until the summer of 2024, it will no doubt bring a few solemn memories back for the Red Devils after their failure of bringing him to Old Trafford.

More specifically, Muller could have become a Red Devil in the summer of both 2015 and 2016, with reports suggesting that the Premier League side were willing to spend £84m to bring him to Old Trafford under the tutelage of van Gaal. However, the German - or more specifically his wife - were not for moving to England according to the former United boss.

As quoted by SportBild, Van Gaal said previously: "I tried to bring Muller to Manchester both in the 2014/2015 season and in the 2015/2016 season. In 2015 it would have been possible if his wife had been a little more open to a transfer abroad.

"At least that was the reason Thomas gave my assistant Marcel Bout, who had had all the conversations with him, why the transfer had been rejected."

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Now with Muller extending his deal, the Red Devils can certainly reflect on some disappointing business having failed to secure his signature. Since those initial links, he has gone on to score 106 goals for Bayern, as well as provide a further 138 assists.

That form has hugely helped the Bavarian giants to continue their relentless pursuit of silverware. Muller now has 12 Bundesliga titles to his name, two Champions Leagues - as well as a World Cup. He was pivotal to Bayern's recent treble secured in the 2019/20 campaign.

That is certainly a winning habit that Manchester United could have done with over the past few seasons. Since lifting their last trophy - the 2017 Europa League title under Jose Mourinho - Muller has collected nine winners' medals.

What will certainly hurt United even more severely though is that United did turn to van Gaal's former club Bayern for a raid - though Muller was overlooked. Germany icon Schweinsteiger was recruited instead for a reported fee of £14.5m.

Despite arriving at Old Trafford with a lofty reputation, the veteran midfielder did not live up to the billing as a Red Devil. Schweinsteiger was only at United for a season-and-a-half before he left for MLS outfit Chicago Fire.

In that time, he made 35 appearances - only 23 of those being starts. He eventually retired from the game in 2019 following three seasons in the United States - all the while Muller remained at the peak of the game with Bayern.

In announcing the extended contract, Muller hailed the glorious period that he has enjoyed at the Allianz Arena, whilst he is eyeing yet more success. As quoted by the German side's official website, he said: "I'm delighted to have extended my contract with FC Bayern Munich until 2024 today.

"The journey we've been on since I joined the FCB academy in 2000 has been a fantastic success story up to now. It gives me immense pleasure to hold up the red colours year after year, on and off the pitch - even if the wind blows in your face from time to time. So, let's keep going together!"

Muller looks highly likely to continue adding to his trophy haul having extended his contract and there will most certainly be regret in the corridors of Old Trafford that the German icon is not doing that on the Red Devils' behalf.