After playing at Menlo-Atherton High, Cunningham starred as an outfielder at San Jose State in 1969 & 1970 where he compiled a .332 batting average and set numerous records.  Cunningham began his baseball coaching career at Del Mar High before taking over the women’s softball team at Mission College, where he was named Community College Coach of the Year.  This was followed by a remarkable 21 years at Bellarmine College Prep, where he averaged 25 victories a season and his teams won an unprecedented 34 games in 2005 & 2006. Cunningham coached the Bells to nine WCAL titles and three CCS championships.  In his 38 years of coaching, Cunningham compiled an 823-375 record.

Gary Cunningham was inducted into the San Jose Sports Hall of Fame in 2013.