The boys' varsity basketball team scored an overtime victory with no time remaining against Friends' Central School on January 19, 2008. Kyle Scott '09 hit the winning shot. Emmanuel Tapia '08 led the Cougars with fifteen points, and Tom Wayda '09 contributed thirteen points and ten rebounds. The atmosphere at the game was energetic, with extra enthusiasm provided by George School's Cougar Crazies—a group of students who appear at athletic events sporting forest green shirts and green-and-white face paint to promote positive energy among George School's fans.
 
"I was particularly impressed by the Cougar Crazies, who kept it loud and positive even when the team fell behind by ten points or so in the second half," said mathematics teacher and boys' soccer coach Paul Machemer '65, who attended the event. "The game was an example of high school basketball at its best." Boys' Athletic Director Sean Casey coaches the boys' varsity basketball team, along with assistant coach John Stevens '02. John said, "It was the most exciting game that I have been a part of in years."