The first cricket captain to win the toss in all five Test matches of a five-match Test series was Sir Donald Bradman, the legendary Australian cricketer and captain. This historic achievement occurred during the Ashes series between Australia and England in 1936-1937.

The 1936-1937 Ashes series, also known as the Bodyline series, is one of the most famous and controversial Test series in cricket history. Sir Donald Bradman was the captain of the Australian team, and Douglas Jardine led the English team.

In that series, Bradman won the toss in all five Test matches. His success in winning the toss provided Australia with an advantage, as they had the opportunity to choose whether to bat or bowl first in each match, depending on pitch and weather conditions.

Although Bradman's team won the toss in all five matches, the series was notable for England's implementation of a controversial bowling tactic known as "Bodyline" or "fast leg theory." This tactic involved fast bowlers bowling deliveries directed at the batsman's body with a packed leg-side field, aiming to restrict Bradman's prolific run-scoring ability. The series generated significant controversy and on-field confrontations.

Despite the challenges posed by Bodyline tactics and winning the toss in all five Tests, Australia lost the series 3-2, with England emerging as the victors. This series remains an iconic chapter in cricket history, remembered for its intensity and its impact on the sport's rules and sportsmanship.