Woodlawn High School - Class of 1999 Alumni
Join thousands of alumni from Woodlawn High School and the Class of 1999. Reconnect with classmates, photos, yearbooks, upcoming reunions.
Varsity Football Schedule 2026-27
08/29 vs Marine Leadership Academy
09/05 vs Uplift
09/12 vs Little Village
09/19 vs DuSable
09/26 vs Kelly
10/03 vs Chicago Washington
10/08 vs Back of the Yards College Prep
10/17 vs Gage Park
10/23 vs Julian
09/05 vs Uplift
09/12 vs Little Village
09/19 vs DuSable
09/26 vs Kelly
10/03 vs Chicago Washington
10/08 vs Back of the Yards College Prep
10/17 vs Gage Park
10/23 vs Julian
Upcoming Class of 1999 Reunions
Browse past reunion events and photos for your class here.Past Class of 1999 Reunions
Browse past reunion events and photos for your class here.Class Yearbook
View past yearbooks
Recently joined '99 Classmates
Bree Brown
Class of 1999
Connect with Class of 1999 Classmates
Nearby Woodlawn Classmates
Class of 2001
3 classmates have joined