Stephen Dennis played his high school basketball at B. Reed Henderson high school in West Chester. Stephen was a three-year varsity starter helping to lead his teams to three Ches-Mont League championships.

Stephen joined the 1000 point club during his high school career. He was selected first team All Ches-Mont as a junior and also during his senior year the Daily Local News selected him as the player of the year. During his high school playing career Stephen was a skilled ball handler and prolific scorer from all areas of the basketball court and played tenacious defense for coach Leon Bell.

After his stellar high school basketball career at Henderson, Stephen enrolled at Kutztown University on a basketball scholarship. While at Kutztown, Stephen was a four-year starter making All-PSAC league all four years and rookie of the year his freshman year. During his senior year he averaged 26 points per game and was named Division II National Player of the Year as well as first team All-American. He left his mark at Kutztown as the all time leading scorer (2,406 points), leader in field goals (850), free throws (621), assists (447) and the single season scoring mark (817).

After an illustrious college career, Stephen signed with the Los Angeles Clippers of the NBA and played on their development D league team. In 2011 he started his professional basketball overseas with the Phantoms Graunsweig in the German league. With summer league roster stints playing with the New York Nets, Stephen signed again to play overseas and is currently playing for the Bnei Herzliya team in the Israeli league.