The Edmonton native started in the 1971-72 with the AJHL's Edmonton Maple Leafs, while playing one game in the WCJHL with the Winnipeg Jets. The 1972-73 season allowed Oleschuk to go back to Edmonton to play for the Mets, while in the 1973-74 season, he moved to Saskatchewan to play 10 games with the Prince Albert Raiders in the SJHL, then 11 games for the Swift Current Broncos of the WHL. The 1974-75 season allowed Oleschuk to play for the Lethbridge Broncos of the WCJHL for two games, then his rights sold over to the Saskatoon Blades-- playing 44 games, putting up a 24-12-5 record, then going 7-5 in the playoffs. Oleschuk got WCJHL top goaltender honors for his efforts.
In the 1975 Draft, Oleschuk was drafted 110th overall by the Kansas City Scouts, where he would only play one game in the 1975-76 season for them, a loss. The rest of the 1975-76 season, Oleschuk played in the IHL with the Port Huron Flags for 44 games. The 1976-77 season saw Oleschuk play three games in the CHL for the Oklahoma City Blazers (0-3-0), but spent the majority of the year with the Southern League Baltimore Clippers, finishing with a 15-14-1 record for the season in 30 games, but the team folded before the season ended.
When the Scouts move to Colorado to become the Rockies, Oleschuk's rights went there, too. He would only play two games with the Rockies that year, both loses. The rest of the 1977-78 season, Oleschuk bounced around the minors-- playing nine games with the CHL's Phoenix Roadrunners (2-6-1) before that team folded, 11 games with the Hampton Gulls of the AHL (1-9-1) before they folded, two games with the Philadelphia Firebirds of the AHL (0-1-0), and 13 games with the IHL's Flint Generals to end the year.
The 1978-79 season was a bit more grounded for Oleschuk-- playing with the Rockies for the entire season; getting in 40 games and putting up a 6-19-8 record. Oleschuk would play 12 games for the Rockies in the 1979-80 season (1-6-2), but would spend the rest of the season with the CHL Fort Worth Texans, going 24-14-3 in 43 games. Staying in Fort Worth for the 1980-81 season, Oleschuk went 10-22-1 in 36 games.
It was a short-lived 1981-82 season, as Oleschuk played only seven games all year with the CHL's Dallas Black Hawks, going 2-4-0. The 1982-83 season, Oleschuk played 29 games for the IHL's Peoria Prancers, then one game with the Fort Wayne Komets in the 1983-84 season before he would hang-up this pads for good.
With all the teams folding around him, you may think of him as a kiss of death for some organzations. That said, the well-travelled goalie was able to see North America and experience every kind of setting. He got lost in the shuffle of an expansion team and one that relocated in the NHL; but was able to try and do his best with not-so-good minor league teams, too.