1. George Kalovelonis
George Kalovelonis was mostly a part-time Greek player, who peaked at No. 208. The peaks of his career included playing the 1988 Seoul Olympics, and defeating Roy Emerson in his last career match. There are obviously many circumstances to be considered with this shocking loss of the 12-time Grand Slam winner. At that point, Emerson was already retired for 6 years, and living in Switzerland, he tried out the Gstaad tournament. Emerson, 47-years-old at the time, lost easily to the 24-year old Greek and never played a professional singles match again. Kalovelonis may be considered one of the luckiest players ever. After getting to win over one of the greatest champions of the sport so out of his prime, he also got to go to the Seoul Olympic games. A dream which few athletes with his resume ever get to make a reality.
