Estevan Police Service Chief Rich Lowen is donning the Weyburn Red Wing's jersey after a loss by the Estevan Bruins over the weekend to their Highway 39 rivals.
Lowen and Weyburn Police Service Chief Jamie Blunden have been betting on which team will win more games against the other across the season for the past three years.
Weyburn won all four games so far, marking the first time they won the bet.
The most recent game on Friday had the Bruins drop a 3-2 game on the road.
The two teams play each other two more times this season, with their next matchup on March 15.