Oleksuk attended the University of Minnesota Duluth where he played four seasons (2008-2012) of NCAA college hockey with the Minnesota–Duluth Bulldogs, scoring 45 goals and 70 assists for 155 points, and earning 75 penalty minutes, in 133 games played.
After three seasons within the Sharks organization, Oleksuk left as a free agent to sign a one-year AHL contract with the Hartford Wolf Pack, an affiliate of the New York Rangers on September 2, 2015.[4] In the 2015–16 season with the Wolf Pack, Oleksuk appeared in 67 games recording 7 goals and 22 points in securing a regular role amongst the checking line.
As a free agent in the following off-season, Oleksuk opted to pursue a European career, agreeing to a one-year contract with Italian based HCB South Tyrol, who compete in the Austrian EBEL on July 28, 2016.[5]
After two seasons with Bolzano and three with Graz 99ers, Oleksuk agreed terms with the Sheffield Steelers for the 2021–22 season.[6] After just 5 games with the Steelers, Oleksuk departed Sheffield in October 2021 for personal reasons. He moved back to Austria to sign for EC VSV.[7]
For the 2022–23 season, Oleksuk continued his career in Europe by moving to German third-tier club, Starbulls Rosenheim of the Oberliga.[8]