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Julian Bashir was the captain of the Starfleet Medical Academy racquetball team in 2368. His team won the Sector Championships in his final year. He played against a Vulcan in his final match, however, he found his greatest opponents were the ones with no formal training. At another tournament, he picked up a 5,000-year-old battle warm-up exercise from a top player. According to legend, the warm-up makes the heart a friend to the hand. (DS9: "Rivals")
In 2370, Miles O'Brien built a racquetball court aboard Deep Space 9. Not long after, Quark promoted a "charity match" between O'Brien and Bashir, with an undisclosed amount of the proceeds from wagering going to the Bajoran War Orphans Fund. The match began but was never finished due to disturbances in the Laws of Probability aboard the station. (DS9: "Rivals")
After two months of Keiko O'Brien's absence in early 2371, Miles O'Brien and Julian Bashir had played 70 games of racquetball. By late that year, they were up to 106 games, at which point they changed over to darts. (DS9: "Fascination", "Prophet Motive")