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#8 Manchester United 1 - 3 Barcelona - 2011
Having lost to Barcelona 2-0 in the UEFA Champions League final in 2009, an expectant United fanbase watched on as Rooney and the boys once again went toe-to-toe with the Catalan giants in 2011 final.
Sir Alex Ferguson seemed confident, looked like a man unable to contemplate a second loss, and, though his Manchester United team went into the game as plucky underdogs, the red devils' fanbase was expectant of a result.
It was not to be. A Wayne Rooney strike canceled out Pedro's opener, but goals from Messi and David Villa in the second half meant that England's finest and most supported club were left watching the celebrations from the touch-line for the second time in three years, a real blow for the fans.
#7 The summer transfer window - 2019
Following an abject, lamentable 4-0 defeat against Everton towards the end of the 2018 season new manager Ole Gunnar Solskjaer had strong words for his underachieving squad:
"We can't change the whole squad, it’s one step at a time. I've said all along I’m going to be successful here. There are players there who won't be part of that successful team but there are players there, of course, who will be."
The fans got on-board. Ole was right; for too long big-name players had been allowed to put in sub-par performances and to collect above-average wages at Old Trafford. It was time to usher in a new era at the club, and most fans were excited to see the rebuild.
So, how did it go? ... not well, unfortunately.
The United board coughed up a hefty £55 million for Crystal Palace's Aaron Wan-Bissaka to replace the retired Antonio Valencia, and Harry Maguire joined the club in an £80 million deal from Leicester, which - in turn - saw Chris Smalling shipped off to Roma on loan. Daniel James signed on from Swansea City, enabling Alexis Sanchez to join Inter Milan on loan, too.
However, Zlatan Ibrahimovic had been allowed to leave for the MLS during the 2018 season - he was never replaced. Fellaini went to China - he was never replaced. Ander Herrera ran down his contract and opted for PSG - he was never replaced. Romelu Lukaku joined Inter Milan - he was never replaced. Matteo Darmian went to Parma - was he replaced? No, of course not; and just recently, captain Ashley Young also escaped to Serie A, and fans are justifiably dubious about the arrival of his successor, too.
The board decided not to replace any of those players, despite the fact United's midfield was already short of options and lacking creativity; and they still haven't...
This makes the list because it highlights how inept Clive, Woodward and the Glazer-run boardroom is when it comes to planning for the future and negotiating transfers.
