The Trailways Conference crowned the following Champions during the 2018-19 school year:

Football - Horicon/Hustisford (Large), Lourdes Academy, Johnson Creek, Fall River (Tie, Small)

Volleyball - Randolph (West), Lourdes Academy (East), Williams Bay (South), Lourdes Academy (Tournament)

Cross Country - Dodgeland (Girls), Parkview (Boys)

Wrestling Duals - Markesan (North), Dodgeland (South)

Wrestling Tournament - Johnson Creek

Forensics - Wayland Academy (North), Horicon (South)

Girls Basketball - Markesan (West), Lourdes Academy  (East), Parkview (South)

Boys Basketball - Randolph (West), Lourdes Academy (East), Palmyra-Eagle (South)

Academic Bowl - Markesan

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

Boys Track and Field Dual - Princeton/Green Lake (West), Dodgeland (East), Deerfield (South)

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

Boys Track and Field Conf Meet - Dodgeland

Girls Track and Field Conf Meet - Rio

Golf Division - Markesan (West), Lourdes/Valley (East), ALCS/MCDS (South)

Golf Conference Meet - Abundant Life / Madison Country Day 

Baseball - Markesan (West), Hustisford/Dodgeland (East), Johnson Creek (South)

Softball - Markesan (West), Horicon (East), Johnson Creek (South)