Man Utd left with £84m transfer regret after Louis van Gaal failed to land target twice

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."

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