#2. Jim Courier
Jim Courier was one of the finest tennis players of his generation and is a winner of four Grand Slam titles, having won the Australian Open in 1992 and 1993 and the French Open in 1991 and 1992. Courier has been at the top of the ATP rankings for a total of 58 weeks before the likes of Sampras and Agassi overtook him in 1993.
Despite being a very good hardcourt player, Courier wasn’t able to win a single US Open title with his best performances including a runner-up performance in 1991 and semi-final exits in 1992 and 1995. Courier’s best opportunity to win the US Open came in 1991 as he had not dropped a single set coming into the final against Stefan Edberg. However, the final turned out to be a completely one-sided affair with Edberg thrashing Courier 6-2, 6-4, 6-0.
Both of Courier’s semi-final exits feature four-set defeats to Pete Sampras. In 1992, Sampras beat him 6-1, 3-6, 6-2, 6-2 and in 1995, beat him by a scoreline of 7-5, 4-6, 6-4, 7-5.