The Trailways Conference crowned the following Champions during the 2023-24 school year:

Athletics:
 

Volleyball - Fall River (West), Valley Christian (East), Abundant Life/St Ambrose (South)

Football - Johnson Creek

Boys Cross Country - Pardeeville

Girls Cross Country - Dodgeland

Wrestling (Duals) - Princeton/Green Lake and Parkview/Albany

Wrestling (Tournament) - Markesan

Girls Basketball - Randolph (West), TBD (East), Deerfield (South)

Boys Basketball - Pardeeville and Randolph (West), Lourdes Academy and Oakfield (East), Abundant Life and Deerfield (South)

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

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

Boys Track Conference Meet - Randolph/Cambria-Friesland

Girls Track Conference Meet - Deerfield

Golf - 

Golf Tournament - 

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

Baseball - 

Academics:
 

Academic Bowl - Johnson Creek

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

Forensics - Randolph (North) and Deerfield (South)