The Trailways Conference crowned the following Champions during the 2022-23 school year:

Athletics:
 

Volleyball - Randolph (West), Horicon (East), Abundant Life/St Ambrose (South)

Football - Cambria-Friesland

Boys Cross Country - Pardeeville

Girls Cross Country - Lourdes Academy

Wrestling (Duals) - Markesan (North), Parkview/Albany (South)

Wrestling (Tournament) - Markesan

Girls Basketball -  Randolph (West), Lourdes Academy (East), Deerfield (South)

Boys Basketball - Fall River (West), CWC (East), Deerfield (South)

Boys Track and Field Dual - Randolph/Cambria-Friesland (West), Horicon (East), Deerfield (South)

Girls Track and Field Dual -  Randolph/Cambria-Friesland (West), Dodgeland (East), Deerfield (South)

Boys Track Conference Meet - Randolph/Cambria-Friesland

Girls Track Conference Meet - Randolph/Cambria-Friesland

Golf - Lourdes Academy/Valley Christian (North), Pardeeville (South)

Golf Tournament - Lourdes Academy/Valley Christian

Softball - Oakfield (North), Horicon (South)

Baseball - Markesan (North), Deerfield (South)

Academics:
 

Academic Bowl - Horicon

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

Forensics -  Randolph (North), Deerfield (South)