Strickland is a multiple winner of the prestigious Player of the Year Award, and his career highlights include five wins at the United States Open Nine-ball Championships (tied with Shane Van Boening for the most all time), and the WPA World Nine-ball Championships. Strickland is the only WPA World Nine-ball Champion ever to win the event in consecutive years. He was also an ever-present player for the American team in the annual Mosconi Cup tournament, from its inauguration in 1994, up until 2009.