As each year progressed, a junior and senior class was filled by the original sophomores (and transfer students of the same grade).

Woodstock first fielded varsity teams in each sport for the 1998–1999 school year.

Woodstock High School held its first classes during the academic year of 1996–97.

The football team made it to the state's Elite 8 in 2008 with an 8-5 record and the Sweet 16 in 2009 by going 10-2.

The softball team won the 5AAAAA State Championship in 2006.