| Week | Date | Home | Score | Away | Score | |
| 9 | 10/17/2019 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 48 | Obama SCTE | 0 | |
| 9 | 10/17/2019 | Brookfield Academy | 51 | Hope Christian | 18 | |
| 9 | 10/17/2019 | Greendale | 21 | Whitnall | 27 | 2OT |
| 9 | 10/17/2019 | Milwaukee Bay View/Lifelong Learning | 18 | Milwaukee Washington/Collegiate/Science | 0 | |
| 9 | 10/17/2019 | Milwaukee Riverside/Golda Meir | 35 | Milwaukee South | 7 | |
| 9 | 10/17/2019 | Oak Creek | 6 | Franklin | 49 | |
| 9 | 10/17/2019 | Racine St. Catherine’s | 41 | Kenosha St. Joseph Catholic Academy | 7 | |
| 9 | 10/17/2019 | Regis | 52 | Neillsville/Granton | 8 | |
| 9 | 10/17/2019 | Saint Francis | 12 | Lake Country Lutheran | 35 | |
| 9 | 10/17/2019 | Milwaukee Bradley/Milw Arts | 58 | Milwaukee Madison | 0 | |
| 9 | 10/17/2019 | Milwaukee Hamilton/Audubon | 40 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 14 | |
| 9 | 10/18/2019 | St. John's NW Military Academy | | University School of Milwaukee | | |
| 9 | 10/18/2019 | Abbotsford | | Athens | | |
| 9 | 10/18/2019 | Almond-Bancroft | | Johnson Creek | | |
| 9 | 10/18/2019 | Appleton West | | Appleton East | | |
| 9 | 10/18/2019 | Aquinas | | Luther | | |
| 9 | 10/18/2019 | Arcadia | | Richland Center | | |
| 9 | 10/18/2019 | Ashland | | Rhinelander | | |
| 9 | 10/18/2019 | Assumption | | Owen-Withee | | |
| 9 | 10/18/2019 | Badger | | Waterford | | |
| 9 | 10/18/2019 | Baldwin-Woodville | | Somerset | | |
| 9 | 10/18/2019 | Baraboo | | Mount Horeb/Barneveld | | |
| 9 | 10/18/2019 | Barron | | Spooner | | |
| 9 | 10/18/2019 | Bay Port | | Pulaski | | |
| 9 | 10/18/2019 | Beaver Dam | | Sauk Prairie | | |
| 9 | 10/18/2019 | Black River Falls | | Wisconsin Dells | | |
| 9 | 10/18/2019 | Blair-Taylor | | Pepin/Alma | | |
| 9 | 10/18/2019 | Bonduel | | Southern Door | | |
| 9 | 10/18/2019 | Boscobel | | Potosi/Cassville | | |
| 9 | 10/18/2019 | Brillion | | New Holstein | | |
| 9 | 10/18/2019 | Brodhead/Juda | | McFarland | | |
| 9 | 10/18/2019 | Brookfield East | | Germantown | | |
| 9 | 10/18/2019 | Brookwood | | Highland | | |
| 9 | 10/18/2019 | Cadott | | Boyceville | | |
| 9 | 10/18/2019 | Cameron | | Bloomer | | |
| 9 | 10/18/2019 | Cashton | | Bangor | | |
| 9 | 10/18/2019 | Catholic Central | | Racine Lutheran | | |
| 9 | 10/18/2019 | Catholic Memorial | | Waukesha North | | |
| 9 | 10/18/2019 | Cedarburg | | West Bend East | | |
| 9 | 10/18/2019 | Clintonville | | Oconto Falls | | |
| 9 | 10/18/2019 | Cochrane-Fountain City | | Augusta | | |
| 9 | 10/18/2019 | Coleman | | Rosholt | | |
| 9 | 10/18/2019 | Columbus | | Poynette | | |
| 9 | 10/18/2019 | Crandon | | Niagara/Goodman/Pembine | | |
| 9 | 10/18/2019 | Cumberland | | Hayward/La Courte Oreilles | | |
| 9 | 10/18/2019 | D.C. Everest | | Stevens Point | | |
| 9 | 10/18/2019 | Darlington | | Cuba City | | |
| 9 | 10/18/2019 | De Pere | | Ashwaubenon | | |
| 9 | 10/18/2019 | De Soto | | Kenosha Christian Life | | |
| 9 | 10/18/2019 | Deerfield | | Lourdes Academy | | |
| 9 | 10/18/2019 | DeForest | | Waunakee | | |
| 9 | 10/18/2019 | Delavan-Darien | | Wilmot Union | | |
| 9 | 10/18/2019 | Dominican | | Shoreland Lutheran | | |
| 9 | 10/18/2019 | Durand | | Mondovi | | |
| 9 | 10/18/2019 | Eau Claire North | | River Falls | | |
| 9 | 10/18/2019 | Edgerton | | Big Foot | | |
| 9 | 10/18/2019 | Eleva-Strum | | Whitehall | | |
| 9 | 10/18/2019 | Elkhorn | | Burlington | | |
| 9 | 10/18/2019 | Ellsworth | | Osceola | | |
| 9 | 10/18/2019 | Elmwood/Plum City | | Unity | | |
| 9 | 10/18/2019 | Evansville | | Clinton | | |
| 9 | 10/18/2019 | Fall River/Rio | | Menominee Indian | | |
| 9 | 10/18/2019 | Fennimore | | Iowa-Grant | | |
| 9 | 10/18/2019 | Flambeau | | Turtle Lake | | |
| 9 | 10/18/2019 | Fort Atkinson | | Oregon | | |
| 9 | 10/18/2019 | Fox Valley Lutheran | | Xavier | | |
| 9 | 10/18/2019 | Gale-Ettrick-Trempealeau | | Adams-Friendship | | |
| 9 | 10/18/2019 | Gilman | | Loyal | | |
| 9 | 10/18/2019 | Glenwood City | | Elk Mound | | |
| 9 | 10/18/2019 | Grantsburg | | Lake Holcombe/Cornell | | |
| 9 | 10/18/2019 | Green Bay Southwest | | Sheboygan North | | |
| 9 | 10/18/2019 | Hillsboro | | Royall | | |
| 9 | 10/18/2019 | Horicon/Hustisford | | Dodgeland | | |
| 9 | 10/18/2019 | Howards Grove | | Ozaukee | | |
| 9 | 10/18/2019 | Hudson | | Chippewa Falls | | |
| 9 | 10/18/2019 | Hurley | | Marathon | | |
| 9 | 10/18/2019 | Independence/Gilmanton | | Melrose-Mindoro | | |
| 9 | 10/18/2019 | Iola-Scandinavia | | Amherst | | |
| 9 | 10/18/2019 | Janesville Parker | | Beloit Memorial | | |
| 9 | 10/18/2019 | Jefferson | | Whitewater | | |
| 9 | 10/18/2019 | Kaukauna | | Hortonville | | |
| 9 | 10/18/2019 | Kenosha Bradford/Reuther | | Racine Park | | |
| 9 | 10/18/2019 | Kettle Moraine | | Arrowhead | | |
| 9 | 10/18/2019 | Kettle Moraine Lutheran | | Berlin | | |
| 9 | 10/18/2019 | Kewaskum | | Ripon | | |
| 9 | 10/18/2019 | Kewaunee | | Peshtigo | | |
| 9 | 10/18/2019 | Kiel | | Two Rivers | | |
| 9 | 10/18/2019 | Kimberly | | Appleton North | | |
| 9 | 10/18/2019 | Kohler/Sheboygan Lutheran/Sheboygan Christian | | Oostburg | | |
| 9 | 10/18/2019 | La Crosse Logan | | Tomah | | |
| 9 | 10/18/2019 | Laconia | | Mayville | | |
| 9 | 10/18/2019 | Ladysmith | | Saint Croix Falls | | |
| 9 | 10/18/2019 | Lakeland | | Wausau East | | |
| 9 | 10/18/2019 | Lakeside Lutheran | | Lodi | | |
| 9 | 10/18/2019 | Lancaster | | Mineral Point | | |
| 9 | 10/18/2019 | Little Chute | | Denmark | | |
| 9 | 10/18/2019 | Madison East | | Verona | | |
| 9 | 10/18/2019 | Madison Memorial | | Janesville Craig | | |
| 9 | 10/18/2019 | Manitowoc Lincoln | | Notre Dame | | |
| 9 | 10/18/2019 | Manitowoc Lutheran | | Mishicot | | |
| 9 | 10/18/2019 | Marinette | | Freedom | | |
| 9 | 10/18/2019 | Markesan | | Pardeeville | | |
| 9 | 10/18/2019 | Marquette | | West Allis Hale | | |
| 9 | 10/18/2019 | Marshall | | Winnebago Lutheran | | |
| 9 | 10/18/2019 | Marshfield | | Sparta | | |
| 9 | 10/18/2019 | Mauston | 1 | Westfield | 0 | Forfeit |
| 9 | 10/18/2019 | Menasha | | Green Bay East | | |
| 9 | 10/18/2019 | Menomonee Falls | | Hamilton | | |
| 9 | 10/18/2019 | Menomonie | | Eau Claire Memorial | | |
| 9 | 10/18/2019 | Merrill | | Medford | | |
| 9 | 10/18/2019 | Middleton | | Madison La Follette | | |
| 9 | 10/18/2019 | Milwaukee King | | Milwaukee Reagan | | |
| 9 | 10/18/2019 | Monroe | | Edgewood | | |
| 9 | 10/18/2019 | Mosinee | | Antigo | | |
| 9 | 10/18/2019 | Mukwonago | | Waukesha West | | |
| 9 | 10/18/2019 | Neenah | | Fond du Lac | | |
| 9 | 10/18/2019 | Nekoosa | | Wautoma | | |
| 9 | 10/18/2019 | New Berlin Eisenhower | | Greenfield | | |
| 9 | 10/18/2019 | New Berlin West | | South Milwaukee | | |
| 9 | 10/18/2019 | New Glarus/Monticello | | Belleville | | |
| 9 | 10/18/2019 | New Lisbon | | Necedah | | |
| 9 | 10/18/2019 | New London | | Seymour | | |
| 9 | 10/18/2019 | New Richmond | | Amery | | |
| 9 | 10/18/2019 | Nicolet | | Homestead | | |
| 9 | 10/18/2019 | North Fond du Lac | | Saint Mary's Springs | | |
| 9 | 10/18/2019 | Northland Pines | | Crivitz | | |
| 9 | 10/18/2019 | Northwestern | | Chetek-Weyerhaeuser | | |
| 9 | 10/18/2019 | Oconomowoc | | Wauwatosa East | | |
| 9 | 10/18/2019 | Omro | | Lomira | | |
| 9 | 10/18/2019 | Onalaska | | Holmen | | |
| 9 | 10/18/2019 | Oshkosh North | | Oshkosh West | | |
| 9 | 10/18/2019 | Osseo-Fairchild | | Fall Creek | | |
| 9 | 10/18/2019 | Palmyra-Eagle | | Montello/Green Lake/Princeton | | |
| 9 | 10/18/2019 | Pecatonica/Argyle | | Black Hawk/Warren IL | | |
| 9 | 10/18/2019 | Pewaukee | | Milwaukee Lutheran | | |
| 9 | 10/18/2019 | Pius XI Catholic | 12 | Brown Deer | 14 | |
| 9 | 10/18/2019 | Platteville | | Prairie du Chien | | |
| 9 | 10/18/2019 | Port Washington | | Hartford Union | | |
| 9 | 10/18/2019 | Portage | | Reedsburg | | |
| 9 | 10/18/2019 | Racine Case | | Kenosha Indian Trail | | |
| 9 | 10/18/2019 | Racine Horlick | | Kenosha Tremper | | |
| 9 | 10/18/2019 | Randolph | | Cambria-Friesland | | |
| 9 | 10/18/2019 | Random Lake | | Cedar Grove-Belgium | | |
| 9 | 10/18/2019 | Reedsville | | Hilbert | | |
| 9 | 10/18/2019 | Rib Lake/Prentice | | Auburndale | | |
| 9 | 10/18/2019 | Rice Lake | | Superior | | |
| 9 | 10/18/2019 | River Ridge | | Southwestern | | |
| 9 | 10/18/2019 | River Valley | | Dodgeville | | |
| 9 | 10/18/2019 | Riverdale | | North Crawford | | |
| 9 | 10/18/2019 | Saint Croix Central | | Prescott | | |
| 9 | 10/18/2019 | Saint Thomas More | | Martin Luther | | |
| 9 | 10/18/2019 | Shawano | | Green Bay West | | |
| 9 | 10/18/2019 | Sheboygan Falls | | Chilton | | |
| 9 | 10/18/2019 | Sheboygan South | | Green Bay Preble | | |
| 9 | 10/18/2019 | Slinger | | Whitefish Bay | | |
| 9 | 10/18/2019 | Spencer/Columbus Catholic | | Altoona | | |
| 9 | 10/18/2019 | Spring Valley | | Colfax | | |
| 9 | 10/18/2019 | Stanley-Boyd | | Colby | | |
| 9 | 10/18/2019 | Stoughton | | Monona Grove | | |
| 9 | 10/18/2019 | Stratford | | South Beloit, IL | | |
| 9 | 10/18/2019 | Sturgeon Bay | 0 | Oconto | 1 | Forfeit |
| 9 | 10/18/2019 | Sun Prairie | | Madison West | | |
| 9 | 10/18/2019 | Thorp | | Greenwood | | |
| 9 | 10/18/2019 | Tomahawk | | Edgar | | |
| 9 | 10/18/2019 | Turner | | East Troy | | |
| 9 | 10/18/2019 | Union Grove | | Westosha Central | | |
| 9 | 10/18/2019 | Valders | | Roncalli | | |
| 9 | 10/18/2019 | Viroqua | | Westby | | |
| 9 | 10/18/2019 | Waterloo | | Cambridge | | |
| 9 | 10/18/2019 | Watertown | | Milton | | |
| 9 | 10/18/2019 | Watertown Luther Prep | | Lake Mills | | |
| 9 | 10/18/2019 | Waukesha South | | Muskego | | |
| 9 | 10/18/2019 | Waupun | | Plymouth | | |
| 9 | 10/18/2019 | Wausau West | | Wisconsin Rapids Lincoln | | |
| 9 | 10/18/2019 | Wauwatosa West | | Brookfield Central | | |
| 9 | 10/18/2019 | Wauzeka-Steuben/Seneca | | Kickapoo/La Farge | | |
| 9 | 10/18/2019 | Webster | | Clear Lake | | |
| 9 | 10/18/2019 | West Allis Central | | Shorewood/Messmer | | |
| 9 | 10/18/2019 | West Bend West | | Grafton | | |
| 9 | 10/18/2019 | West De Pere | | Waupaca | | |
| 9 | 10/18/2019 | West Salem | | La Crosse Central | | |
| 9 | 10/18/2019 | Weyauwega-Fremont | | Shiocton | | |
| 9 | 10/18/2019 | Wild Rose | | Pacelli | | |
| 9 | 10/18/2019 | Winneconne | | Campbellsport | | |
| 9 | 10/18/2019 | Wisconsin Lutheran | | Cudahy | | |
| 9 | 10/18/2019 | Wittenberg-Birnamwood | | Manawa | | |
| 9 | 10/18/2019 | Wonewoc-Center/Weston | | Ithaca | | |
| 9 | 10/18/2019 | Wrightstown | | Luxemburg-Casco | | |
| 9 | 10/19/2019 | Living Word Lutheran | | Parkview/Albany | | |