The general received training in F-105 Thunderchiefs at Nellis Air Force Base, Nevada, and was assigned to the 8th Tactical Fighter Squadron, Spangdahlem Air Base, West Germany, where he flew F-105s from October 1965 to January 1967. General Cherry then transferred to Korat Royal Thai Air Force Base, Thailand, and while serving with the 421st and 44th Tactical Fighter squadrons, completed 100 combat missions over North Vietnam. In August 1967 he became an F-105 instructor pilot and flight examiner with the 23rd Tactical Fighter Wing, McConnell Air Force Base, Kansas.
In June 1971 the general returned to Thailand, where he served with the 13th Tactical Fighter Squadron, Udorn Royal Thai Air Force Base, and completed 185 combat missions flying F-4D Phantoms. During this tour of duty, General Cherry served as flight commander and chief of the 432nd Tactical Fighter Wing “Laredo” F-4 foward air controller program. He also was credited with the destruction of a North Vietnamese MIG-21.