Cheshire High School - Class of 1999 Alumni
Join thousands of alumni from Cheshire High School and the Class of 1999. Reconnect with classmates, photos, yearbooks, upcoming reunions.
Varsity Football Schedule 2026-27
09/10 vs West Haven
09/17 vs Glastonbury
09/24 vs Notre Dame‑West Haven
10/01 vs Staples
10/08 vs Daniel Hand
10/22 vs Jonathan Law
10/29 vs Fairfield Prep
11/05 vs Sheehan
11/12 vs Guilford
11/25 vs Southington
09/17 vs Glastonbury
09/24 vs Notre Dame‑West Haven
10/01 vs Staples
10/08 vs Daniel Hand
10/22 vs Jonathan Law
10/29 vs Fairfield Prep
11/05 vs Sheehan
11/12 vs Guilford
11/25 vs Southington
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
Connect with Class of 1999 Classmates
Nearby Cheshire Classmates
Class of 1997
13 classmates have joined
Class of 1998
14 classmates have joined
Class of 2000
8 classmates have joined
Class of 2001
11 classmates have joined