Chiles High School Timberwolves Spring 2026 Schedule
| Time | Away | Home | Location | |||
| Mon, 2/2/26 to Sun, 2/8/26Week 1 | ||||||
| Tuesday, February 3, 2026 | ||||||
| 3:00 pm | Chiles Varsity | vs. | South Walton | South Walton HS | ||
| 5:30 pm | Chiles Varsity | vs. | Pace | South Walton HS | ||
| Mon, 2/9/26 to Sun, 2/15/26Week 2 | ||||||
| Tuesday, February 10, 2026 | ||||||
| 6:00 pm | Buchholz | vs. | Chiles Varsity | Chiles High School | ||
| Friday, February 13, 2026 | ||||||
| 6:00 pm | Chiles Varsity | vs. | Venice | Venice High School | ||
| Saturday, February 14, 2026 | ||||||
| 2:00 pm | Chiles Varsity | vs. | Sarasota | Sarasota High School | ||
| Mon, 2/16/26 to Sun, 2/22/26Week 3 | ||||||
| Tuesday, February 17, 2026 | ||||||
| 6:00 pm | Lincoln | vs. | Chiles Varsity | Chiles High School | ||
| Wednesday, February 18, 2026 | ||||||
| 5:30 pm | Chiles Junior Varsity | vs. | Florida High | Florida High | ||
| Thursday, February 19, 2026 | ||||||
| 7:30 pm | Chiles Varsity | vs. | Niceville High | Niceville High | ||
| Friday, February 20, 2026 | ||||||
| 5:00 pm | Chiles Junior Varsity | vs. | Niceville High | Niceville High | ||
| Saturday, February 21, 2026 | ||||||
| 5:30 pm | Chiles Varsity | vs. | Oakleaf | Valdosta High School | ||
| Mon, 2/23/26 to Sun, 3/1/26Week 4 | ||||||
| Monday, February 23, 2026 | ||||||
| 4:30 pm | Chiles Junior Varsity | vs. | Lowndes Co. | Lowndes Co. HS | ||
| 7:00 pm | Chiles Junior Varsity | vs. | Lowndes Co. | Lowndes Co. HS | ||
| Tuesday, February 24, 2026 | ||||||
| 6:00 pm | NFC Eagles | vs. | Chiles Varsity | Chiles High School | ||
| Wednesday, February 25, 2026 | ||||||
| 4:00 pm | Chiles Junior Varsity | vs. | Lincoln JV | Chiles High School | ||
| 6:00 pm | Choctawhatchee | vs. | Chiles Varsity | Chiles High School | ||
| 6:30 pm | Chiles Junior Varsity | vs. | Lincoln JV | Chiles High School | ||
| Friday, February 27, 2026 | ||||||
| 4:00 pm | Suwannee (Live Oak) | vs. | Chiles Junior Varsity | Chiles High School | ||
| 7:00 pm | Suwannee | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 3/2/26 to Sun, 3/8/26Week 5 | ||||||
| Tuesday, March 3, 2026 | ||||||
| 6:00 pm | Mosley HS | vs. | Chiles Varsity | Chiles High School | ||
| Thursday, March 5, 2026 | ||||||
| 4:30 pm | Chiles Junior Varsity | vs. | Columbia | Columbia High School | ||
| 7:00 pm | Chiles Varsity | vs. | Columbia | Columbia High School | ||
| Friday, March 6, 2026 | ||||||
| 4:00 pm | Menendez | vs. | Chiles Junior Varsity | Chiles High School | ||
| 7:00 pm | Menendez | vs. | Chiles Varsity | Chiles High School | ||
| Saturday, March 7, 2026 | ||||||
| 12:00 pm | Bishop Kenny | vs. | Chiles Varsity | Chiles High School | ||
| 2:30 pm | Bishop Kenny | vs. | Chiles Junior Varsity | Chiles High School | ||
| Mon, 3/9/26 to Sun, 3/15/26Week 6 | ||||||
| Tuesday, March 10, 2026 | ||||||
| 4:30 pm | Chiles Varsity | vs. | Leon High School | Leon High School | ||
| 5:00 pm | Leon High School | vs. | Chiles Junior Varsity | Chiles High School | ||
| Wednesday, March 11, 2026 | ||||||
| 4:00 pm | Chiles Junior Varsity | vs. | Suwannee | Suwanee High School | ||
| 7:00 pm | Chiles Varsity | vs. | Suwanee | Suwanee High School | ||
| Thursday, March 12, 2026 | ||||||
| 4:30 pm | Thomas Central HS | vs. | Chiles Junior Varsity | Chiles High School | ||
| 7:00 pm | Thomas Central HS | vs. | Chiles Junior Varsity | Chiles High School | ||
| Friday, March 13, 2026 | ||||||
| 4:00 pm | North Marion HS | vs. | Chiles Varsity | Chiles High School | ||
| Mon, 3/16/26 to Sun, 3/22/26Week 7 | ||||||
| Tuesday, March 17, 2026 | ||||||
| 7:00 pm | Chiles Varsity | vs. | Silverdale Academy (TN) | PC Publix Park | ||
| Wednesday, March 18, 2026 | ||||||
| 7:00 pm | Chiles Varsity | vs. | Lakeside School (AL) | PC Publix Park | ||
| Mon, 3/23/26 to Sun, 3/29/26Week 8 | ||||||
| Monday, March 23, 2026 | ||||||
| 4:30 pm | Chiles Junior Varsity | vs. | Wakulla HS | Wakulla High School | ||
| 7:00 pm | Chiles Junior Varsity | vs. | Wakulla HS | Wakulla High School | ||
| Tuesday, March 24, 2026 | ||||||
| 6:30 pm | Chiles Varsity | vs. | Wakulla HS | Wakulla High School | ||
| Wednesday, March 25, 2026 | ||||||
| 4:30 pm | Chiles Junior Varsity | vs. | Thomas Central HS | Thomas County Central High School | ||
| 7:00 pm | Chiles Junior Varsity | vs. | Thomas Central HS | Thomas County Central High School | ||
| Thursday, March 26, 2026 | ||||||
| 4:00 pm | Chiles Varsity | vs. | NFC | North Florida Christian | ||
| Saturday, March 28, 2026 | ||||||
| 12:00 pm | South Walton | vs. | Chiles Varsity | Chiles High School | ||
| 3:00 pm | Lincoln JV | vs. | Chiles Junior Varsity | Chiles High School | ||
| Mon, 3/30/26 to Sun, 4/5/26Week 9 | ||||||
| Tuesday, March 31, 2026 | ||||||
| 4:30 pm | Lowndes Co. JV | vs. | Chiles Junior Varsity | Chiles High School | ||
| 7:00 pm | Lowndes Co. JV | vs. | Chiles Junior Varsity | Chiles High School | ||
| Wednesday, April 1, 2026 | ||||||
| 5:00 pm | Houston County (GA) | vs. | Chiles Varsity | Chiles High School | ||
| Thursday, April 2, 2026 | ||||||
| 4:30 pm | Maclay HS | vs. | Chiles Junior Varsity | Chiles High School | ||
| Friday, April 3, 2026 | ||||||
| 6:00 pm | Chiles Varsity | vs. | Pace | Pace High School | ||
| 7:00 pm | Chiles Junior Varsity | vs. | Leon High School | Leon High School | ||
| Saturday, April 4, 2026 | ||||||
| 12:00 pm | Lincoln JV | vs. | Chiles Junior Varsity | Chiles High School | ||
| 12:00 pm | Chiles Varsity | vs. | Pensacola Catholic | Pensacola Catholic High School | ||
| 2:30 pm | Lincoln JV | vs. | Chiles Junior Varsity | Chiles High School | ||
| Mon, 4/6/26 to Sun, 4/12/26Week 10 | ||||||
| Wednesday, April 8, 2026 | ||||||
| 6:00 pm | Florida High | vs. | Chiles Varsity | Chiles High School | ||
