| Skyway Classic Criterium Series | Chicago, IL | 4/1/2019- 4/4/2019 | Criterium |
| Rough Road 100 | Morris, IL | 4/6/2019 | Gravel |
| Return to the Hills Cross Race | Rockford, IL | 4/6/2019 | Cyclocross |
| Sylvan Island Stampede | Moline, IL | 4/7/2019 | Mountain/Fat Bike |
| Spring Super Criterium | South Beloit, IL | 4/7/2019 | Criterium |
| John Fraser Memorial TT | Winfield, IL | 4/7/2019 | Tri/Duathlon |
| Barry Roubaix | Hastings, MI | 4/13/2019 | Gravel |
| Dairy Roubaix | Bagley, WI | 4/20/2019 | Gravel |
| Another Dam Cross Race | Rockford, IL | 4/20/2019 | Cyclocross |
| Grumpy Grind | Milledgeville, IL | 4/27/2019 | Gravel |
| Cherry Valley 20k Time Trial | Cherry Valley, IL | 4/28/2019 | Tri/Duathlon |
| Lincoln Park Criterium | Chicago, IL | 4/28/2019 | Criterium |
| La Crosse Omnium - Time Trial | La Crosse, WI | 5/3/2019 | Criterium |
| Ride the Ups and Downs | Elizabeth, IL | 5/4/2019 | Road/General |
| La Crosse Omnium - Crit | La Crosse, WI | 5/5/2019 | Criterium |
| Screw City Duathlon | Loves Park, IL | 5/5/2019 | Tri/Duathlon |
| Englewood Open | Fall River, WI | 5/5/2019 | Mountain/Fat Bike |
| Illiniwek Abermination | Hampton, IL | 5/5/2019 | Mountain/Fat Bike |
| Watertown Duathlon | Watertown, WI | 5/6/2019 | Tri/Duathlon |
| Region Riot | Hammond, IN | 5/11/2019 | Criterium |
| Neenah Duathlon | Neenah, WI | 5/12/2019 | Tri/Duathlon |
| Harvard Time Trial 33.3k | Harvard, IL | May (TBD) | Tri/Duathlon |
| First Thaw Tri | Oconomowoc, WI | 5/18/2019 | Tri/Duathlon |
| Iola Bump & Jump | Iola, WI | 5/19/2019 | Mountain/Fat Bike |
| Hop On: Tailwind Dive Bar Tour | Oregon, IL | May (TBD) | Road/General |
| Arlington 500 | Lake County, IL | May (TBD) | Road/General |
| Capitol View Triathlon & Duathlon | Madison, WI | May (TBD) | Tri/Duathlon |
| Burlington Road Race | Mediapolis, IA | 5/24/2019 | Road/General |
| Blackhawk Country Roads | Rockford, IL | 5/25/2019 | Road/General |
| Snake Alley Criterium | Burlington, IA | 5/25/2019 | Criterium |
| Midwest Gravel Championship and WBR Ride | Dekalb, IL | 5/25/2019 | Gravel |
| Ten Thousand | Freeport, IL | 5/26/2019 | Gravel |
| Melon City Criterium | Muscatine, IA | 5/26/2019 | Criterium |
| Kwik Star Criterium | Davenport, IA | May (TBD) | Criterium |
| BayCare Clinic Century | Green Bay, WI | 6/1/2019 | Road/General |
| Battle of CamRock | Rockdale, WI | 6/2/2019 | Mountain/Fat Bike |
| Fox Lake Triathlon | Fox Lake, IL | 6/2/2019 | Tri/Duathlon |
| Lake Mills Triathlon | Lake Mills, WI | 6/2/2019 | Tri/Duathlon |
| Fight For Air! | Crystal Lake, IL/WI | June (TBD) | Road/General |
| Tour Of the Mississippi River Valley | Quad Cities, IA/IL | 6/7/2019- 6/9/2019 | Touring |
| 70.3 Wisconsin | Madison, WI | 6/9/2019 | Tri/Duathlon |
| ET Batavia Sprint Triathlon and Duathlon | Batavia, IL | 6/9/2019 | Tri/Duathlon |
| Ramble Ride | Wilmot, WI | 6/9/2019 | Road/General |
| XTERRA Illinois Wilds Tri | Hanna City, IL | 6/9/2019 | Tri/Duathlon |
| Grand Illinois Bike Tour | Clinton, IL | 6/9/2019- 6/14/2019 | Touring |
| Chicago Honor Ride | Skokie, IL | June (TBD) | Road/General |
| Gran Fondue Balloon & Blues Festival | Monroe, WI | June (TBD) | Road/General |
| Horribly Hilly Hundreds | Blue Mounds, WI | 6/15/2019 | Road/General |
| Rock River Adventure Tri | Oregon, IL | 6/15/2019 | Tri/Duathlon |
| Pie Ride | Janesville, WI | 6/15/2019 | Road/General |
| Lake in the Hills Triathlon | Palatine, IL | 6/16/2019 | Tri/Duathlon |
| Mount Morris Challenge | Mt Morris, WI | 6/16/2019 | Mountain/Fat Bike |
| RAIL (Ride Across Illinois) North | Moline, IL | 6/16/2019 | Touring |
| Kenosha YMCA Food, Folks & Spokes | Kenosha, WI | 6/20/2019 | Criterium |
| East Troy Cycling Classic | East Troy, WI | 6/21/2019 | Criterium |
| Giro d Grafton | Grafton, WI | 6/22/2019 | Criterium |
| Hartford Du | Hartford, WI | 6/22/2019 | Tri/Duathlon |
| River District 12 | Rockford, IL | 6/22/2019 | Road/General |
| Bike MS: Tour De Farms | Geneva, IL | 6/22/2019, 6/23/2019 | Road/General |
| Bigfoot Triathlon | Lake Geneva, WI | 6/23/2019 | Tri/Duathlon |
| Twin Lakes Triathlon | Palatine, IL | 6/23/2019 | Tri/Duathlon |
| Red Flint Firecracker | Eau Claire, WI | 6/23/2019 | Mountain/Fat Bike |
| Swedish Days Ride | Hampshire, IL | 6/23/2019 | Road/General |
| Waukesha Carl Zach Cycling Classic | Waukesha, WI | 6/23/2019 | Criterium |
| Downtown West Bend Concourse | West Bend, WI | 6/24/2019 | Criterium |
| Janesville Town Square Gran Prix | Janesville, WI | 6/25/2019 | Criterium |
| Port Washington Race the Harbor | Port Washington, WI | 6/26/2019 | Criterium |
| Shorewood Criterium Cycling Classic | Shorewood, WI | 6/27/2019 | Criterium |
| Swiss Cheese and Spotted Cow | Spring Green, WI | 6/27/2019- 6/30/2019 | Touring |
| Cafe Centraal Bay View Classic | Milwaukee, WI | 6/28/2019 | Criterium |
| Otto Wenz Cafe Hollander Downer Classic | Milwaukee, WI | 6/29/2019 | Criterium |
| Tour Against Cancer | Freeport, IL | 6/29/2019 | Road/General |
| East Tosa Gran Prix | East Tosa, WI | 6/30/2019 | Criterium |
| WORS Cup | Elkhorn, WI | 7/5/2019-7/7/2019 | Mountain/Fat Bike |
| Pewaukee Duathlon | Pewaukee, WI | 7/6/2019 | Tri/Duathlon |
| Lake Zurich Triathlon | Lake Zurich, IL | 7/14/2019 | Tri/Duathlon |
| Fitchburg Festival of Speed | Fitchburg, WI | 7/13/2019 | Criterium |
| Freeport Classic | Freeport, IL | July (TBD) | Tri/Duathlon |
| Tri-State Tour | Tri-State, IL/WI/IN | 7/14/2019 | Road/General |
| Biking with Beanzie | DeKalb, IL | 7/14/2019 | Road/General |
| Bloomington Crit | Bloomingto, IL | July (TBD) | Criterium |
| Beverly Hills Cycling Classic | Chicago, IL | 7/20/2019 | Criterium |
| Z-Tour | Princeton, IL | 7/20/2019 | Road/General |
| Colectivo Coffee Bean Classic | Waukesha, WI | 7/21/2019 | Mountain/Fat Bike |
| Wauconda Triathlon | Wauconda, IL | 7/21/2019 | Tri/Duathlon |
| Lake Bluff Criterium | Lake Bluff, IL | 7/21/2019 | Criterium |
| Ragbrai | Multi, IA | 7/21/2019- 7/27/2019 | Touring |
| Dennis Jurs Memorial Race | Elgin, IL | 7/22/2019 | Criterium |
| Autobahn Country Club Road Race | Joliet, IL | 7/23/2019 | Criterium |
| South Chicago Kermesse Road Race | South Chicago, IL | 7/24/2019 | Criterium |
| West Dundee River Challenge | West Dundee, IL | 7/25/2019 | Criterium |
| Niles Cycling Classic | Niles, IL | 7/26/2019 | Criterium |
| Route 66 Half Iron Triathlon | Springfield, IL | 7/27/2019 | Tri/Duathlon |
| Superior Ambulance Cycling Classic | Elmhurst, IL | 7/27/2019 | Criterium |
| Lake Ripley Ride | Cambridge, WI | 7/27/2019 | Road/General |
| Tour of Lake Ellyn | Glen Ellyn, IL | 7/28/2019 | Criterium |
| Tour De North End | Rockford, IL | 7/20/2019 | Road/General |
| Oregon Park District Triathlon | Oregon, IL | July (TBD) | Tri/Duathlon |
| William Blair Grand Prix | Chicago, IL | 7/29/2019 | Criterium |
| Hixon Forest Epic | La Crosse, WI | 8/4/2019 | Mountain/Fat Bike |
| Naperville Sprint Triathlon | Naperville, IL | 8/4/2019 | Tri/Duathlon |
| Lake Country Triathlon | Oconomowoc, WI | 8/10/2019 | Tri/Duathlon |
| Ride Across Wisconsin | Southern, WI | August (TBD) | Road/General |
| Dairyland Dare | Dodgeville, WI | August (TBD) | Road/General |
| Rotary Ride | Naperville, IL | August (TBD) | Road/General |
| Bicycle Illinois | Multi, IL | 8/17/2019- 8/23/2019 | Touring |
| Ride Like An Egyptian | DeKalb, IL | August (TBD) | Road/General |
| Chicago Triathlon | Chicago, IL | 8/24/2019, 8/25/2019 | Tri/Duathlon |
| Lake Mills Du | Lake Mills, WI | 8/24/2019 | Tri/Duathlon |
| Tri-State Tour | Tri-State, IL/WI/IN | 8/24/2019 | Road/General |
| Reurn to Cherry Valley 20k Time Trial | Cherry Valley, IL | 8/25/2019 | Tri/Duathlon |
| Treadfest | Lake Geneva, WI | 8/25/2019 | Mountain/Fat Bike |
| Race the Lake | Fond du Lac, WI | 8/25/2019 | Road/General |
| Everybody Rides | St Charles, IL | August (TBD) | Road/General |
| Relay Cross | Chicago, IL | August (TBD) | Cyclocross |
| Cycle On 2nd | Rockford, IL | September (TBD) | Road/General |
| Ironman Wisconsin | Madison, WI | 9/8/2019 | Tri/Duathlon |
| Tempo Velo Farmondo | Sterling, IL | 9/8/2019 | Road/General |
| CCC - Hopkins Park | Dekalb, IL | September (TBD) | Cyclocross |
| Harmon Hundred | Wilmot, WI | September (TBD) | Road/General |
| Winfield Criterium | Winfield, IL | September (TBD) | Criterium |
| Fever River Tri | Galena, IL | 9/14/2019 | Tri/Duathlon |
| CCC - Caldwell Woods | Chicago, IL | September (TBD) | Cyclocross |
| Dousman Duathlon | Dousman, WI | 9/21/2019 | Tri/Duathlon |
| Trek Cup | Waterloo, WI | September (TBD) | Cyclocross |
| Fall Fling Crit | Wood Dale, IL | September (TBD) | Criterium |
| Tour of Scenic Ogle County | Oregon, IL | September (TBD) | Road/General |
| Tour De Freeport | Freeport, IL | September (TBD) | Road/General |
| Jingle Cross | Iowa City, IA | September (TBD) | Cyclocross |
| CX Eliminator | Chicago, IL | September (TBD) | Cyclocross |
| Al Stern Marathon Bicycle Road Race | Aroma Park, IL | October (TBD) | Road/General |
| Spotted Horse Gravel Ultra | St Charles, IA | October (TBD) | Gravel |
| CCC - Dan Ryan Woods | Chicago, IL | October (TBD) | Cyclocross |
| Pumpkin Pie Ride | Ottawa, IL | October (TBD) | Road/General |
| Great Apple Ride | Harvard, IL | October (TBD) | Road/General |
| Lemon Lime Duro by TFB | Rockford, IL | October (TBD) | Road/General |
| CCC - Carpentersville | Carpentersville, IL | October (TBD) | Cyclocross |
| CCC - Sunrise Park | Bartlett, IL | October (TBD) | Cyclocross |
| CCC - Campton | Wasco, IL | October (TBD) | Cyclocross |
| Axels at the Castle | Oregon, IL | November (TBD) | Road/General |
| CCC - Wheeling | Wheeling, IL | November (TBD) | Cyclocross |
| CCC - Pheasant Run | St. Charles, IL | November (TBD) | Cyclocross |