Since the 1967 constitution was adopted, only seven different people (all men) have served as Premier or Chief Minister, and each of them except for Cyril Romney and Andrew Fahie has served at least two full terms. Also, each of them has served as the Leader of the Opposition.
H. Lavity Stoutt won the most general elections of any leader (he won five), followed by Orlando Smith (three). Stoutt, Smith and Willard Wheatley are the only leaders to have served two consecutive full terms (Ralph T. O'Neal also served two consecutive terms, but the first of those was the remaining part of a term after Stoutt's death).
List
(Dates in italics indicate de facto continuation of office)
^Duration of terms are calculated as commencing on the date of the election; not the actual subsequent date of appointment by the Governor, which is usually a few days later.
^Wheatley led a coalition of himself plus the VI Democratic Party in the 1971 election and then another coalition of himself plus the United Party in the 1975 election.
References
^While the territory is commonly known as the 'British Virgin Islands', her official name is simply 'Virgin Islands'.