| Electronic Door Locks | Ethan Levy, Logan Rosengard | Glenbrook North HS |
| GNCY Vaping Presentation | Ethan Levy, Logan Rosengard | Glenbrook North HS |
| Bagel Creation | Ethan Levy, Chris Fabbioli | Glenbrook North HS |
| Coach Purdy | Ethan Levy, Stella Balaskas | Glenbrook North HS |
| Dan Briggs | Ethan Levy, Stella Balaskas | Glenbrook North HS |
| Hidden Gem | Lilly Donkel, Caroline Johnson | Homewood-Flossmoor |
| HP150 Time Capsule | Stephen Knobel | Highland Park HS |
| HPHS Israeli Culture Day 2020 | Stephen Knobel | Highland Park HS |
| MHH ESPYS – Performance of the Year | Tyler Hopton | William Mason HS |
| MHS ESYYS – Upset of the Year | Morgan Scholz | William Mason HS |
| Nihilistic Yearbook Ads | Jared Goudsmit, Eli Boshara | Kirkwood HS |
| Traveling Show | Ethan Levy, Julia Foster | Glenbrook North HS |
| Walk of Hope 2019 | Ben Turnquest, Langston Johnson | Homewood-Flossmoor |
