In 2005, the high school grades began and in 2009, Oakwood graduated its first senior class.

Oakwood's Space Systems Engineering class has received notable recognition, with students appearing in an interview on KTVU FOX 2.

[4] Oakwood offers Varsity and JV sports including Basketball, Volleyball, Soccer, Cross Country, Track and Field, Tennis, Wrestling, Golf, and Swimming, and participates in the Mission Trail Athletic League (MTAL).

Oakwood plays competitively in several sports, and advances to the Central Coast Section (CCS) playoffs regularly.

The Varsity Boys Basketball program won the school’s first CCS team championship in 2023 and advanced to the Elite Eight in the State of California.