| Day | Date | Time | Event | Location | Notes | Links |
|---|---|---|---|---|---|---|
| Tue. | August 3, 2021 | 6:00 | Football Team Media Day | Paul Brown Tiger Stadium | ||
| Thu. | August 5, 2021 | Sideliners' Reverse Raffle | ||||
| Sat. | August 7, 2021 | 11:30 am | Scrimmage vs. Avon (Freshmen start at 9:00 am) | Avon High School | ||
| Sun. | August 8, 2021 | 1:00 pm | Sideliners Picnic | WHS | ||
| Thu. | August 12 , 2021 | 2:00 pm | Scrimmage vs. Cincinnati St. Xavier (JV and Freshmen start at 12:00 noon) | Cincinnati | ||
| Sat. | August 14, 2021 | 1:00 pm | Alumni Association Golf Scramble | Elms Country Club | Shotgun start | |
| Tue. | August 17, 2021 | 11:30 am | First Touchdown Club Luncheon | Massillon Eagles | Memberships for the year are available at the door | |
| Wed. | August 18, 2021 | 6:30 pm | Downtown Kickoff Rally | Duncan Plaza | ||
| Fri. | August 20, 2021 | 7:30 pm | Season Opener vs. Pickerington Central | Paul Brown Tiger Stadium | ||
| Mon. | August 23, 2021 | 7:00 pm | First Booster Club Meeting | WHS | ||
| Thu. | October 20, 2021 | 6:00 pm | High School Open House | Washington High School | ||
| Fri. | October 21, 2021 | 7:00 pm | Beat McKinley Parade | Downtown Massillon | ||
| Sat. | October 22, 2021 | 2:00 pm | Season Finale vs. Canton McKinley | Canton's Benson Stadium | ||
| ? | ? | ? | Football Banquet | |||
| Past Events | ||||||
| Thu. | May 6, 2021 | 6:00 pm | College Football Showcase | WHS Indoor Facility | Registration at 5:00 pm | |
| Fri. | May 7, 2021 | ? | Monte Carlo Night | Overtime Bar & Grill | Details | |
| Sat. | June 26, 2021 | Noon to 4:00 pm | Tiger Moms Car Wash | O'Reilly Auto Parts | ||
| Sat. | May 8, 2021 | 6:00 pm | Steve Studer Memorial Lift-a-Thon | WHS | Registration at 5:15 pm | |
| Tue. | June 29, 2021 | Noon | 7 on 7 Passing Scrimmage | Paul Brown Tiger Stadium | ||
| Sat. | July 10, 2021 | 8:30 am to 10:30 am | Tiger Moms 5K Run | Parking at the movie theater |