2025-2026
CHILES HIGH SCHOOL FOOTBALL
Chiles Timberwolves Fall 2025 Schedule
| Time | Away | Home | Location | |||
| Mon, 7/28/25 to Sun, 8/3/25Week 1 | ||||||
| Monday, July 28, 2025 | ||||||
| 7:30 am - 10:00 am | First Day of Fall Football | Chiles High School | ||||
| 6:00 pm | PARENT MEETING | Chiles High School | ||||
| Tuesday, July 29, 2025 | ||||||
| 7:30 am - 10:00 am | FALL PRACTICE | Chiles High School | ||||
| 5:00 pm | VARSITY PHOTO DAY | Chiles High School | ||||
| Wednesday, July 30, 2025 | ||||||
| 7:30 am - 10:00 am | FALL PRACTICE | Chiles High School | ||||
| 5:00 pm | JR VARSITY PHOTO. DAY | Chiles High School | ||||
| Thursday, July 31, 2025 | ||||||
| 6:00 am - 8:30 am | FALL PRACTICE | Chiles High School | ||||
| Mon, 8/11/25 to Sun, 8/17/25Week 2 | ||||||
| Thursday, August 14, 2025 | ||||||
| 6:00 pm | Spaghetti Kick-Off Dinner | Chiles Cafeteria | ||||
| Friday, August 15, 2025 | ||||||
| 7:00 pm | Kick Off Classic | Chiles High School | ||||
| Varsity | ||||||
| 7:00 pm | Booker T. Washington (Pensacola) | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 8/18/25 to Sun, 8/24/25Week 3 | ||||||
| Thursday, August 21, 2025 | ||||||
| JV | ||||||
| 6:30 pm | Lincoln High School | vs. | Chiles JV | Chiles High School | ||
| Friday, August 22, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Chiles Varsity | vs. | Dothan | Dothan High School | ||
| Mon, 8/25/25 to Sun, 8/31/25Week 4 | ||||||
| Wednesday, August 27, 2025 | ||||||
| JV | ||||||
| 6:30 pm | Chiles JV | vs. | Rickards JV | Rickards High School | ||
| Friday, August 29, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Pelham | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 9/1/25 to Sun, 9/7/25Week 5 | ||||||
| Thursday, September 4, 2025 | ||||||
| JV | ||||||
| 6:30 pm | Leon JV | vs. | Chiles JV | Chiles High School | ||
| Friday, September 5, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Chiles Varsity | vs. | Wakulla High School | Wakulla High school | ||
| Mon, 9/8/25 to Sun, 9/14/25Week 6 | ||||||
| Thursday, September 11, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Godby JV | vs. | Chiles JV | Chiles High School | ||
| Friday, September 12, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Rickards High School | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 9/15/25 to Sun, 9/21/25Week 7 | ||||||
| Thursday, September 18, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Chiles JV | vs. | Lincoln JV | Lincoln High School | ||
| Friday, September 19, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Chiles Varsity | vs. | Godby High School | Gene Cox Stadium | ||
| Mon, 9/22/25 to Sun, 9/28/25Week 8 | ||||||
| Wednesday, September 24, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Wakulla | vs. | Chiles JV | Chiles High School | ||
| Thursday, September 25, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Impact Christian Academy | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 9/29/25 to Sun, 10/5/25Week 9 | ||||||
| Thursday, October 2, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Rickards JV | vs. | Chiles JV | Chiles High School | ||
| Friday, October 3, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Chiles Varsity | vs. | Florida High School | Florida High School | ||
| Mon, 10/6/25 to Sun, 10/12/25Week 10 | ||||||
| Wednesday, October 8, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Chiles JV | vs. | Leon JV | Leon High School | ||
| Friday, October 10, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Lincoln High School | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 10/13/25 to Sun, 10/19/25Week 11 | ||||||
| Wednesday, October 15, 2025 | ||||||
| JV | ||||||
| 6:00 pm | Chiles JV | vs. | Godby JV | Godby High School | ||
| Friday, October 17, 2025 | ||||||
| —:— — | VARSITY BYE WEEK | |||||
| Mon, 10/20/25 to Sun, 10/26/25Week 12 | ||||||
| Thursday, October 23, 2025 | ||||||
| —:— — | JV BYE WEEK | |||||
| Friday, October 24, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Chiles Varsity | vs. | Leon High School | Gene Cox Stadium | ||
| Mon, 10/27/25 to Sun, 11/2/25Week 13 | ||||||
| Thursday, October 30, 2025 | ||||||
| Varsity | ||||||
| 7:00 pm | Suwannee High School | vs. | Chiles Varsity | Chiles High School | ||
