Winchester High School - Class of 1999 Alumni
Join thousands of alumni from Winchester High School and the Class of 1999. Reconnect with classmates, photos, yearbooks, upcoming reunions.
Varsity Football Schedule 2026-27
09/09 vs Lynn Classical
09/17 vs Acton‑Boxborough
09/24 vs Masconomet Regional
10/01 vs Melrose
10/08 vs Reading Memorial
10/15 vs Arlington
10/21 vs Lexington
10/29 vs Belmont
11/25 vs Woburn Memorial
09/17 vs Acton‑Boxborough
09/24 vs Masconomet Regional
10/01 vs Melrose
10/08 vs Reading Memorial
10/15 vs Arlington
10/21 vs Lexington
10/29 vs Belmont
11/25 vs Woburn Memorial
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
Michelle Breen
Class of 1999
Connect with Class of 1999 Classmates
Nearby Winchester Classmates
Class of 1997
12 classmates have joined
Class of 1998
16 classmates have joined
Class of 2001
7 classmates have joined