After taking the place of winger Gerry Bridgwood in the first team, he made an instant impact on his debut on 6 September 1967, by scoring the winning goal in a 3–2 victory over Leicester City at the Victoria Ground. Though Conroy only made nine league appearances in the 1967–68 season, he was present on the final day 2–1 win over Liverpool which kept Stoke out of the First Division relegation zone. He was again registered with the Cleveland Stokers – now in the North American Soccer League – in the summer of 1968, but did not play a first team game for the club. He started to become a first team regular for Stoke in the 1968–69 season after scoring against Liverpool at Anfield on 20 August, and went on to score in four consecutive games over the Christmas period. Waddington did though sometimes prefer to play John Mahoney to Conroy, using Mahoney as an extra defensive midfielder to make Stoke more solid defensively. Conroy also damaged cartilage in his knee after being challenged heavily by Manchester City's left-half Alan Oakes in a 3–1 defeat at Maine Road on 29 March, and was ruled out of action for five months. After recovering he went on to make 33 appearances in the 1969–70 campaign, and got some measure of revenge over Manchester City at Maine Road on 17 January by scoring the only goal of the game after dribbling past three defenders from the half-way line.