He was selected for the tour of the West Indies in 1983–84 as deputy keeper to Wayne Phillips. He played only the Fourth Test in St John's, keeping wickets when Phillips opened the innings, but he scored only 13 and 8 in an innings defeat for Australia. At the time the Australian journalist Peter McFarline said his wicketkeeping "generally was again a long way short of the standard necessary." He had his most successful season with the bat in 1984–85, scoring 717 runs at 51.21, including his highest first-class score of 144 (and 61 in the second innings) against Western Australia in Perth. But, captaining a Tasmanian side that won none of its ten matches and finished last in the Shield, the quality of Woolley's keeping deteriorated. John MacKinnon in "Wisden" noted that "his wicket-keeping was erratic and his captaincy was inhibited by lack of confidence in his team". He played the rest of his career as a batsman, retiring after two matches in 1987–88. Woolley was captain of the Tasmanian one-day side from 1982–83 until 1985–86, and although he also captained the first-class side on 28 occasions, he was never officially appointed as Tasmanian captain. He later made his career in real estate. He regularly provides comments on ABC radio broadcasts of matches in Tasmania.