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Thanks to this form, May extended his contract at St Johnstone until 2015. He then scored four goals in three matches against Motherwell, Hearts and Kilmarnock.
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In a match against Inverness CT on 5 October, May provided a triple assist and scored, as St Johnstone won 4–0. New St Johnstone manager Tommy Wright described him as "heading for the top". He scored 4 goals in his first 9 games of the season leading to a call-up for the Scotland U21 team. He went on to score the winner against Hearts, and goals against Ross County and Hibs. Awarded a starting place, he scored the equaliser against Europa League opponents, Rosenborg, in a famous 2–1 aggregate win. May started the 2013–14 season very well. May believed his performance in his two loan spells would allow him to make a breakthrough at the club. Immediately after being linked with Peterborough, May was offered and signed a further contract extension by St Johnstone. In the summer of 2013 May was the subject of several bids from Peterborough United of the English League One, though May insisted he was happy at the club. His future at St Johnstone appeared to be in doubt, but he signed a new one-year contract in May 2013. At the end of the season, May was awarded again when he won Irn-Bru SFL Phenomenal Young player of the Season. At the end of the season, May says he enjoyed his time at Hamilton. For his performance in April, May was awarded the Irn Bru player and young player of the month in the Scottish Football League. After scoring fifteen goals this season, May scored two consecutive hat tricks, against Airdieonians, in a 5–0 win on 11 April 2013 and another against Livingston, in a 3–0 win on 18 April 2013. May cited moving to Hamilton on loan, as "get his own career back on track." After four games without a goal, May scored his first goal and then another in the match, in addition to two assists, as Hamilton beat Airdrieonians 4–0 on 11 October 2012. On 29 August 2012, he joined Scottish First Division side Hamilton Academical on loan until. May signed a new one-year contract with St Johnstone. At the end of the season, May won the Irn-Bru SFL Phenomenal Third Division Player of the Season. He scored four goals in the 8–1 victory against Elgin City that clinched the Third Division championship. May was awarded the SFL Player of the Month, Young Player of the Month and Irn-Bru Ginger Boot awards for January the first time that one player has won all three player awards in a month. After one month at the club, May had his loan spell with Alloa extended until the end of the season. He made his league debut for Alloa on 10 December against Queen's Park, going on to score his first goals on 2 January 2012, netting a hat-trick for The Wasps in a 3–1 win against East Stirlingshire. With appearances limited he was loaned to Alloa Athletic until the end of January. May's only appearance of the 2011–12 season for St Johnstone came as a substitute on the opening day of the season against Aberdeen at Pittodrie. In all he made 22 appearances that season scoring twice. He scored two goals on 1 February 2011 in their 2–0 win over Hamilton. With his first start coming on 26 January 2011 against Motherwell. May had to wait another season for his next appearance, coming on as a substitute on 13 November 2010 against Hearts in the Scottish Premier League. He taught me how important it was to keep possession when I had the ball and make the opposition work to get it back." In 2009, he signed a new contract that tied him to the club until 2012. May later recalled on his debut, quoting: " Derek McInnes gave me my first taste of first team football. Aged 16, May made his first team debut on as a substitute against Airdrie United in the Scottish First Division scoring his first senior goal. May began playing football aged ten and started his career as a member of St Johnstone's youth squad.