Wednesday, May 27
| Time | Description | Location |
| 6:00 PM | FCA DINNER - Hot Dog Feed and Ice Cream Social Badges Required Open to all athletic participants | Woodward County Fair Building |
| 11:00 PM | CURFEW - ALL PARTICIPANTS |
Thursday, May 28
| Time | Description | Location |
| 9:00 AM | BOYS BASKETBALL REGISTRATION | Boomer Field House |
| 9:30 AM | Boys Basketball Coaches Orientation | Boomer Field House |
| 10:00 AM | Boys Basketball Practice | |
| 12:00 PM | Basketball Lunch | K-101 Radio Station Suite S |
| 1:30 PM | Boys Basketball Practice | |
| 4:00 PM | Basketball Pre-Game meal | K-Bob's |
| 5:30 PM | Basketball Photo Session | Boomer Field House |
| 6:30 PM | Classic Bowl Boys Basketball - Game 1 Badge Required | Boomer Field House |
| Red 1 vs. White 1 | ||
| 8:00 PM | Classic Bowl Boys Basketball - Game 2 Badge Required | Boomer Field House |
| Red 2 vs. White 2 | ||
| 11:00 PM | CURFEW - ALL PARTICIPANTS |
Friday, May 29
| Time | Description | Location |
| 7:00 PM | ATHLETIC AWARDS BANQUET Advanced Ticket Purchase Required (open to public), Drew Williams Scholarship Award, Athletic Awards | Woodward High School Commons Area |
| 9:00-11:30 PM | 101 CLASSIC BOWL MIXER 101 Classic Bowl Participants Only Badges Required | 101 Centre/K-101 Studios |
| 12:00 AM | CURFEW - ALL PARTICIPANTS |
Saturday, May 30
| Time | Description | Location |
| 1:30 PM | PARADE STAGING | 16th & Main |
| 2:00 PM |
101 Classic Bowl XXI Parade |
Downtown Woodward |
| 8:00 PM | 101 CLASSIC BOWL XXI GAME | Woodward Boomer Stadium |
| Half-time | Scholarship Awards Presentation: Cheerleader, Basketball, Band & Football | Woodward Boomer Stadium |
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