The Trailways Conference crowned the following Champions during the 2020-21 school year:

Softball - 

Baseball - 

Golf Tournament - 

Golf - 

Boys Track Conference Meet - 

Girls Track Conference Meet - 

Boys Track and Field Dual - 

Girls Track and Field Dual -  

Academic Bowl - Markesan

Math Meet - 

Girls Basketball -  Randolph (West), Oakfield (East), Palmyra-Eagle (South)

Boys Basketball - Randolph (West), Lourdes Academy (East), Williams Bay (South)

Forensics - Markesan (North), Deerfield (South)

Football - Lourdes Academy

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

Volleyball (Alternate Fall) - Parkview and Princeton/Green Lake