In 2011 a couple of rival buddies got together over drinks to kick around the idea of having Hilton Head's elite compete in what has become HHIPL – Hilton Head Island Pro League. When Lee, who had already been playing in a pro league in Charleston, presented the idea to Matt, he immediately got the ball rolling! The two men credit Dwight Trew of Coral Resorts as the title sponsor and the first to step up to support the league. Patrick Mason of Wexford wasted no time and got on board early to gather numerous sponsors, also becoming one of the league's first captains. South Beach's Don & Rachael Sigmon were instrumental in the success of the league's first match as their facility hosted the event. As its founding president, Lee Holyoak sums up Pro League to “promote tennis, raise money, and have some competition!” With the standard format of Court 1, 2 and 3 doubles, and 2 rounds of matches, there is enough high-quality tennis for all to see. Since 2011 The Pro League has donated to the PTR International Wheelchair Championships. In 2017 Matt and Lee passEd on the duties of league administration to Mike Pollard and Tom Ruth. The Watanabe Cup was introduced in 2019 and given to the championship team each year. The trophy is named after former WTA player and long time pro league player Jolene Watanabe.
