Thomas of Woodstock, 1st Duke of Gloucester (~1385), 1st Earl of Buckingham (1377), 1st Earl of Essex, [1385 Duke of Aumale] KG (7 January 1355 – 8 or 9 September 1397)
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, fourth son of King Henry IV.
The title was next conferred on Richard, brother to King Edward IV. When Richard himself became king, the dukedom merged into the crown. After Richard III's death, the title was considered ominous, since the first three such dukes had all died without issue to inherit their titles. The title was not awarded for over 150 years: the next to receive the dukedom was the son of King Charles I, Henry Stuart, upon whose death the title again became extinct.
The first four creations were in the Peerage of England and the last in the Peerage of the United Kingdom
https://en.wikipedia.org/wiki/Duke_of_Gloucester#First_creation,_1385%E2%80%931397 .