On May 26, 1994, after shooting and killing his family at home, a 17-year-old student held his classroom hostage at gunpoint for 30 minutes before releasing them and surrendering to the police, after being persuaded to do so by vice principal Steve Sorrell.

The school also offers honors courses, with the intent of challenging students and preparing them for post-secondary education.

The Ryle Raider boys' 2002 basketball team won Districts and the 9th Region tournament to gain a place in the Sweet 16 at Rupp Arena.

For the first time in school history the boys' basketball team made it to Lexington to battle for the State Championship.

[citation needed] The Ryle Lady Raiders won the program's first Regional Championship in 2018 and made it to the KHSAA Elite 8.

In football, the Ryle Raiders were state runners-up in 2006, losing the final game to Trinity High School (Louisville).

The Ryle Marching Band has appeared in the Kentucky Music Educators Association (KMEA) State Finals eight times (2001, 2002, 2017, 2019, 2021, 2022, 2023, 2024).