The Trailways Conference crowned the following Champions during the 2019-20 school year:

Football - Horicon/Hustisford (Large), Lourdes Academy (Small)

Volleyball - Fall River (West), Lourdes Academy (East), Johnson Creek (South), Fall River (Tournament)

Cross Country - Lourdes Academy (Girls), Parkview (Boys)

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

Wrestling Tournament - Markesan

Forensics - Wayland Academy (North), Johnson Creek (South)

Girls Basketball - Fall River (West), Oakfield (East), Deerfield (South)

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

The remainder of the events/seasons were cancelled due to the COVID-19 pandemic.