In 1964–65, Simpson led Australia on a tour of the Caribbean, which was marred by controversies over umpiring standards and the legality of West Indian Charlie Griffith's bowling action. To make life more difficult, some of the grounds had no sightscreens, making it even harder to see the ball. Griffith also dragged his foot, bringing him around a metre closer to the batsman before releasing his balls at extreme pace. Simpson initially struggled against Griffith, failing to pass 30 in the first three Tests as Australia conceded a 0–2 lead. He scored only 87 in five innings, but had success with the ball, capturing 4/83 in the second innings of the Second Test at Trinidad. Adjusting his technique, Simpson scored 201 in the Fourth Test at Barbados, where he set an Australian record opening stand of 382 with Lawry. The match was drawn, but Australia managed a consolation win in the Fifth Test, to which Simpson contributed 72 and 34 not out. His average for 399 runs was 49.88 and he took 11 catches. Simpson made his displeasure regarding Griffith known to the Australian board, and this was relayed to the West Indian administrators.