2007-08: Drew Olson completed his senior year at Brainerd High School, where he was a finalist for Minnesota’s Mr. Hockey award, and selected a second team All-State defenseman. Olson was a leader on his team both offensively and defensively. He played on the team’s top pairing and was one of the top defensemen in Minnesota.
2008-09: Olson played 39 games in the USHL with the Omaha Lancers. He scored 2 goals, 6 assists for 8 points along with 43 PIMs.
2009-10: Olson received consistent ice time as a freshman for the University of Minnesota-Duluth. He skated in 34 games and notched 2 assists.
2010-11: Olson skated in 34 of 42 games for NCAA national champion Minnesota-Duluth as a sophomore – missing time due to a lower body injury. Paired with fifth-year senior Trent Palm for much of the second half, the two combined to give the Bulldogs a steady third pair. Olson scored 1 goal with 3 assists and was +3 with 18 PMs.
2011-12: In his junior season at Minnesota-Duluth, Olson set up seven goals and put one in himself. He doubled his point totals from his sophomore year and has become known as a defensive defenseman more than anything else.
2012-13: Olson made his pro hockey debut with the AHL's Peoria Rivermen following his senior season at Minnesota-Duluth. In five games with Peoria he had 1 assist and was -2 with 2 penalty minutes. Olson skated in 38 games for the Bulldogs as a senior in what was a disappointing season in Duluth. He scored 1 goal with 6 assists and was -15 with 28 penalty minutes. Two years removed from winning the national championship, UM-D struggled for much of the season, finishing ninth in the WCHA, and was swept by Wisconsin in the first round of the WCHA tournament. The Bulldogs failed to win 20 games for the first time since 2007-08. Not tendered a contract by Columbus, he was invited to Tampa Bay's training camp and signed an AHL contract with Syracuse in September of 2013.
A solidly-built defenseman, more wide than tall, Olson is a very good skater who has a very good shot from the point. He is tough to beat one-on-one, and often punishes players who try to beat him wide. He has a very good presence on the point with his shot that can anchor a power play. Olson needs to work on his conditioning and to improve his overall strength.
Olson was dealt by the Columbus Blue Jackets to the Tampa Bay Lightning in July of 2013. He signed an AHL contract for the 2013-14 season.