The title was first conferred on Thomas of Woodstock, the thirteenth child of King Edward III. The title became extinct at his death, as it did upon the death of the Duke of the second creation, Humphrey of Lancaster, fifth son of King Henry IV.
The title was next conferred on Richard Plantagenet, brother to King Edward IV. When Richard himself became King, the dukedom merged into the crown. Next to receive the dukedom was the son of King Charles I, Henry Stuart, upon whose death the title became extinct.
William, son of Queen Anne, was styled "Duke of Gloucester" for his whole life (1689-1700), but never created as such.
The next actual creation was for the brother of George III, Prince William Henry, the full title being "Duke of Gloucester and Edinburgh".
The fifth and final creation was for Prince Henry, son of King George V. Upon Prince Henry's death, the dukedom was inherited by his son Prince Richard, who still holds the title. The heir to the title is presently Alexander Windsor, styled Earl of Ulster.
Dukes of Gloucester, first Creation (1385)
Dukes of Gloucester, second Creation (1414)
Dukes of Gloucester, third Creation (1461)
Dukes of Gloucester, fourth Creation (1659)
Dukes of Gloucester and Edinburgh (1764)
Dukes of Gloucester, fifth Creation (1928)