The Caribou Cup is awarded annually to the school that performs the best across the board in CTL competition.
In each sport, points are awarded based on the CTL regular season finish of all teams in the league. The CTL champion receives 5 points and the runner-up receives 4 points with the next team down receiving 3 points. The process continues until all teams have been awarded points. In the event of a tie, each tied team receives the average of the sum of the spots for which they are competing.
After the total points are calculated, points are then divided by the number of CTL sports that each school participates in to arrive at an average score.
The Caribou Cup standings are updated each season before a winner is announced following the spring sports season. The winner keeps the traveling trophy at their school the following school year. The award was established prior to the 2017-2018 school year.