Following his graduation, Oleksy turned professional to join the Las Vegas Wranglers for two games at the end of their 2008–09 ECHL season.

[2] Proving a solid addition to the Sound Tigers' defense, Oleksy was signed as a free agent for the following 2012–13 season in the AHL with the Hershey Bears on July 2, 2012.

[5] On July 1, 2015, Oleksy left the Capitals as a free agent and signed a one-year, two-way contract with the Pittsburgh Penguins.

On March 1, 2017, Oleksy was included in a trade by the Penguins, alongside Eric Fehr and a fourth-round pick in 2017, to the Toronto Maple Leafs in exchange for Frank Corrado.

[9] During the second year of his contract in the 2018–19 season, while with the Ducks AHL affiliate, the San Diego Gulls, Oleksy was traded for a second time to the Toronto Maple Leafs in exchange for Adam Cracknell on December 10, 2018.

On September 27, 2019, he agreed to return to former AHL club the Wilkes-Barre/Scranton Penguins, signing an initial professional tryout contract to begin the 2019–20 season.

[12] Oleksy made 36 appearances in his return with the Walleye before leaving North America to sign a contract in Europe for the remainder of the season with Austrian club, EHC Black Wings Linz of the EBEL, on February 7, 2020.