Middlesboro High School - Class of 1999 Alumni
Join thousands of alumni from Middlesboro High School and the Class of 1999. Reconnect with classmates, photos, yearbooks, upcoming reunions.
Varsity Football Schedule 2026-27
08/21 vs Breathitt County
09/03 vs Garrard County
09/10 vs Leslie County
09/17 vs Cloudland
09/24 vs Lynn Camp
10/01 vs Harlan
10/08 vs Pineville
10/15 vs Williamsburg
10/22 vs Harrison County
10/29 vs Sayre
09/03 vs Garrard County
09/10 vs Leslie County
09/17 vs Cloudland
09/24 vs Lynn Camp
10/01 vs Harlan
10/08 vs Pineville
10/15 vs Williamsburg
10/22 vs Harrison County
10/29 vs Sayre
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
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Class of 1997
10 classmates have joined
Class of 1998
12 classmates have joined
Class of 2000
13 classmates have joined
Class of 2001
6 classmates have joined