2026 Winter Flag Football - San Jose - Willow Glen High School
Welcome to the 7th season of Next Level Flag Football at Willow Glen High School in San Jose! We are excited to keep things rolling with Coach Oscar Caballero and the entire staff at Willow Glen High School.
General Registration is now open for all participants!
For more information and a general overview of our specific Next Level Flag Football location at Willow Glen High School, please review the information below prior to registration!
League Operations
- Season Operations: The Next Level Flag Football season at Willow Glen High School will run with 9 program dates over the program schedule.
- Game Dates: Most games are on Sundays - check the schedule below for details!
- Team Roster Size: Teams are comprised of 10 players maximum, limited exceptions on a case-by-case basis.
- Season Fees: $315.00 Fees are inclusive of a participant's custom jersey, shorts, use of flags, and other equipment/offerings.
- Uniform Delivery: All season uniforms will be shipped to a participant's home (or provided shipping address). Delivery will occur via USPS and a valid USPS delivery location is required. Participants must keep their shipping addresses up to date for proper delivery. Replacement uniforms will be at the cost of the participant should inaccurate addresses be provided at the time of production.
- Player Packs - Optional Purchases: During the registration process, you will have the opportunity to purchase any of our five (5) additional Next Level Flag Football Player Packs. These are optional purchases to go along with your program registration fees. Player Pack items will be added to your base league fees (which include the cost of your participant’s uniform) at checkout. All Player Pack merchandise will be shipped directly to your home along with your participant’s season uniform - unless otherwise communicated from our team. Sizing verifications (where applicable) will be sent out via email as your uniform heads into production!
- Receiver Gloves - $40.00: Nike Vapor Jet Receiver Gloves.
- Base Player Pack - $45.00: Nike Long Sleeve Dri-Fit featuring our Player Logo (front) and participant’s last name (back).
- Pro Player Pack - $60.00: Nike Hoodie featuring our Player Logo (front) and participant’s last name (back).
- Performance Pack - $65.00: One pair of 3/4 Compression Tights (white), one Compression Shirt (white).
- Baller Player Pack - $190.00: ALL OF THE ABOVE - Receive Gloves, Base Pack, Pro Pack, and Performance Pack all in one! Get DIALED IN…
Practice & Game Times
- Kindergarten - 8:30 AM Practice/9:00 AM Game
- 1st Grade - 9:00 AM Practice/10:00 AM Game
- 2nd Grade - 10:00 AM Practice/11:00 AM Game
- 3rd Grade - 11:00 AM Practice/12:00 PM Game
- 4th Grade - 12:00 PM Practice/1:00 PM Game
- 5th Grade - 1:00 PM Practice/2:00 PM Game
- 6th Grade - 2:00 PM Practice/3:00 PM Game
- 7th/8th Grade - 3:00 PM Practice/4:00 PM Game
Please see here for facility information.
Game Schedule
| Week 1 | Sunday, January 11th |
| Week 2 | Sunday, January 18th |
| Week 3 | Sunday, January 25th |
| Week 4 | Sunday, February 1st |
| Week 5 | Saturday, February 7th (Super Bowl Weekend) |
| Week 6 | Sunday, February 15th |
| Week 7 | Sunday, February 22nd |
| Week 8 | Sunday, March 1st (Playoffs) |
| Week 9 | Sunday, March 8th (Championship Weekend) |
All teams will play games through the entire 9-week program schedule regardless of their seeding in the Playoff Weeks. Schedule above may be subject to change.
General Program Operation and Additional Information
Review the general program operations, program information and philosophies of the Next Level Flag Football program - CLICK HERE TO REVIEW
Site Director: Oscar Caballero
Coach Oscar Caballero began his football career in 1990 at Mt. Pleasant High School playing alongside his twin brother, Andre. Oscar won a full ride football scholarship to Montana State in 1996 where he played under former Alabama OC and Florida HC Jim Mcelwain. For the last decade Oscar has acted as the Head Varsity Football Coach at Willow Glen High School. Accolades include San Francisco 49’ers’ Coach of the Week in 2014 and the Offensive Coordinator at the Charlie Wedemeyer All Star Game in 2012. Outside of his joy in his long running football career, Oscar prides himself on raising two fantastic sons, Kai and Kion, with his wife Parisa.