The Trailways Conference crowned the following Champions during the 2021-22 school year:

Softball - 

Baseball - 

Golf Tournament - 

Golf - 

Boys Track Conference Meet - Deerfield

Girls Track Conference Meet - Dodgeland

Boys Track and Field Dual - 

Girls Track and Field Dual -  

Academic Bowl - 

Math Meet - 

Girls Basketball -  

Boys Basketball - 

Wrestling Tournament - 

Wrestling Duals - Markesan (North)

Forensics -

Football - Lourdes Academy

Volleyball Tournament - Randolph (Gold), Horicon (Silver), Markesan (Bronze)

Volleyball - Randolph (West), CWC (East), Johnson Creek (South)

Cross Country - Pardeeville (Boys), Lourdes Academy (Girls)