#2 Jim Courier
Former World Number 1 Jim Courier had a remarkable season in 1991. Winning the French Open for the first time, Courier beat defending champion Pete Sampras in straight sets in his quarter-final match at the US Open. He then went on to beat another American - crowd favourite 39-year old Jimmy Connors in the semi-finals. Beating two 5-time US Open champions on back-to-back occasions made his stock rise and he was the overwhelming favourite to clinch his maiden US Open title and his second Grand Slam overall. But it all unravelled for him in the finals, where he crumbled under pressure losing to Swede Stefan Edberg in straight sets.
In the final, Courier just managed to win a paltry six games. This was Courier's best chance to win at Flushing Meadows. He would go on to win 3 more Grand Slam titles but never crossed the semis at the US Open ever again.