Winter Springs High School - Class of 1999 Alumni
Join thousands of alumni from Winter Springs High School and the Class of 1999. Reconnect with classmates, photos, yearbooks, upcoming reunions.
Varsity Football Schedule 2026-27
08/20 vs Lake Howell
08/30 vs Hagerty
09/03 vs Melbourne
09/09 vs New Smyrna Beach
09/17 vs Lyman
10/01 vs Ridge Community
10/08 vs Bishop Moore
10/15 vs Seabreeze
10/21 vs Deltona
10/29 vs Davenport
08/30 vs Hagerty
09/03 vs Melbourne
09/09 vs New Smyrna Beach
09/17 vs Lyman
10/01 vs Ridge Community
10/08 vs Bishop Moore
10/15 vs Seabreeze
10/21 vs Deltona
10/29 vs Davenport
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.Winter Springs '99 Apparel
Browse our apparel store for a wide range of Bears gear, from t-shirts and hoodies, to caps and accessories.
Class Yearbook
View past yearbooks
Connect with Class of 1999 Classmates
Nearby Winter Springs Classmates
Class of 1998
3 classmates have joined
Class of 2000
57 classmates have joined
Class of 2001
72 classmates have joined