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

Softball - Oakfield (North), Johnson Creek (South)

Baseball - Markesan (North), Johnson Creek, Palmyra-Eagle, Deerfield (South)

Golf Tournament - ALCS/MCDS/SAA

Golf - Lourdes/Valley (North), ALCS/MCDS/SAA (South)

Boys Track Conference Meet - Deerfield

Girls Track Conference Meet - Dodgeland

Boys Track and Field Dual - Fall River (West), Horicon (East), Deerfield (South)

Girls Track and Field Dual -  Rio (West), Dodgeland (East), Deerfield (South)

Academic Bowl - Markesan

Math Meet - CWC (North), Williams Bay (South)

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 (tie)