| Happy No Trails 2021 Opener | 04-24-2021 | 33 | Ultra Event | |
| Chicago Loops (150 - 100) | 06-05-2021 | 13 | Ultra Event | |
| Turtletown Double Century | 05-08-2021 | 11 | Double Century | |
| The Dark Chocolate Cow | 07-03-2021 | 11 | ACP 1000 | |
| Blackhawk Double Century | 09-04-2021 | 7 | Double Century | |
| Nature's Metropolis 140 | 07-18-2021 | 5 | Ultra Event | |
| Dancing Jellyfish Double Century | 06-19-2021 | 5 | Double Century | |
| Dancing Jellyfish 375 | 06-19-2021 | 4 | Ultra Event | |
| Chonkey Chimp 100k | 05-15-2021 | 4 | Gravel | |
| Death's Door Double Century | 07-03-2021 | 4 | Double Century | |
| The Menomonie Ho-Chunk 600k | 07-03-2021 | 3 | ACP 600 | |
| Redbird's Challenge | 07-03-2021 | 3 | Century | |
| Rib Moutain Double Century | 08-07-2021 | 3 | Double Century | |
| High Cliff to the Lake 155 | 06-24-2021 | 2 | Ultra Event | |
| West Loop from Gurnee | 07-04-2021 | 1 | Imperial | |
| The Mini Chocolate Cow | 06-30-2021 | 1 | Ultra Event | |
| Wisconsin Loop Ride | 08-22-2021 | 1 | Imperial | |
| Dancing Jellyfish 125 | 06-20-2021 | 1 | Ultra Event | |
| Circle Tour of NE Lake County | 06-19-2021 | 1 | Imperial | |
| Psychedelic Cow 400k | 06-05-2021 | 1 | ACP 400 | |
| Wisconsin Loop Ride | 02-20-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 02-28-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 02-28-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 03-05-2021 | 1 | Imperial | |
| West Loop from Gurnee | 03-13-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 03-26-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 04-10-2021 | 1 | Imperial | |
| Circle Tour of NE Lake County | 04-11-2021 | 1 | Imperial | |
| Lakes and Kettles 300k | 05-08-2021 | 1 | ACP 300 | |
| Snoopy Loop | 05-27-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 05-31-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 06-01-2021 | 1 | Imperial | |
| Wisconsin Loop Ride | 01-23-2021 | 1 | Imperial | |