In his first year as head coach for the Transcona Railer Express, Derek led the team all the way to the MMJHL finals. The 2017-18 season was the first time the team had made the finals since 1992. Derek's efforts did not going unnoticed, earning him the MMJHL 2017-18 Coach of the Year Award.

Derek's coaching experience includes two seasons with the St. James Canucks and also with minor hockey. 

He finished his playing career for the Selkirk Steelers of the MJHL.