A well traveled Trey Dickerson arrived to Georgetown in the summer of 2017, exercising his fifth year graduate option from the University of South Dakota.

Dickerson averaged 10.4 points per game for the Coyotes in 2016-17, the third leading scorer on a USD team that finished 22-12 and advanced to the school's first NIT bid. Georgetown was the fifth college for the 23 year old guard and the eighth stop in the past nine seasons.

Originally from New York, Dickerson played freshman basketball at Christ the King Academy in Queens Village, NY but struggled academically according to reports, moving to Los Angeles in the 2009-10 season to play for Montclair Prep of Van Nuys but the school closed in 2011. He moved on to Price Christian School in Los Angeles, averaging 14.8 ppg in 2011-12, but then moved on to God's Academy, a basketball-only prep school headquartered in a south Dallas recreation center.

"Dickerson is extremely fast with the ball, and he is even more dangerous in transition," wrote Future150.com in a 2013 review of the two-star rated guard. "His ball-handling is his biggest attribute, but...he needs to work on playing under control and limiting the turnovers."

At God's Academy, Dickerson averaged 23 points per game and qualified for a NCAA Division I scholarship. He committed to Murray State in the summer of 2013, choosing the Racers over offers from the University of Seattle and Oakland University. This proved to be a brief stop, as he decommitted at the close of the summer term and moved to Williston State, a North Dakota junior college. Dickerson earned third team junior college All-America honors with Williston, averaging 19 points and five assists for the Tetons. In 2014-15 he transferred to Iowa, choosing the Hawkeyes over interest from Nebraska, Arkansas, and Washington State, but saw limited action, averaging less than three points per game.

While at Georgetown, Dickerson saw limited time and averaged less than four points entering Big East play. Towards the end of the season, however, Dickerson was more effective, with a season high 18 points against Butler.