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 and Horicon

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

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