Stricker had a memorable 1998 season, not simply for a heroic performance at the PGA Championship where he finished second, one stroke back of Vijay Singh, but also for the birth of his first child. Stricker's first and second PGA Tour wins came in 1996 at the Kemper and Motorola Western Opens. Wife Nicki often served as his caddie and her father, Dennis Tiziani, the golf coach at the University of Wisconsin, is Stricker's teacher. Stricker was an All-American for the University of Illinois in 1988 and 1989.