#3 Jim Courier:
Courier almost always wore a cap on the court, but could not add the Wimbledon title as a feather to it. He was the World No. 1 for 58 weeks and also won 4 Grand Slams in his career, but could not win the Wimbledon.
The closest he got was in 1993, when he lost to Pete Sampras in a classic 4-setter in the final. Courier had a decent serve on him and also a great double-handed backhand, but was a baseliner primarily and did not have the requisite volleying skills to win the title.
Moreover, his career coincided with that of Pete Sampras, arguably the greatest grass-court player of all time. Sampras won the Wimbledon 7 times in 8 years from 1993 to 2000 and virtually owned the hallowed grass-courts during that decade. He beat Courier once in the Wimbledon and was one of the reasons behind the latter’s failure to win the prestigious tournament during the peak of his career.
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