On 20 December, Sterling was named as the recipient of the 2014 Golden Boy award. "It's down to hard work. I'm really happy that people are recognising that I'm trying to work hard and do my best for this football club. I'm really grateful for this award," he stated upon receiving the award. Sterling was officially excused from Liverpool's FA Cup match against AFC Wimbledon in January 2015, with manager Brendan Rodgers aiming to prevent the player becoming exhausted. He used the time off to holiday in Jamaica.
On 20 January 2015, Sterling scored a fine solo goal against Chelsea in a 1–1 draw in the League Cup semi-final first leg at Anfield, going past Nemanja Matić and Gary Cahill before beating Thibaut Courtois to find the net. On 31 January, Sterling scored the opening goal in a 2–0 win over West Ham United. On 4 February, Sterling scored the equaliser against Bolton Wanderers at the Macron Stadium in a 1–2 away win for Liverpool. On 22 February, he scored the second goal for Liverpool in a 0–2 win over Southampton.
On 13 April, Sterling opened the scoring in a 2–0 win over Newcastle United. He was named the team's Young Player of the Season on 19 May for the second consecutive year in a row, and when receiving the award was booed by fans due to his rejection of a new contract; he was also booed on 7 June, while playing for England in Dublin. On 16 April 2015, for the second consecutive year, he was named as one of the six players on the shortlist for the PFA Young Player of the Year award.
On 9 February 2015, Brendan Rodgers said that Sterling had been offered "an incredible deal" to stay at Liverpool, rumoured to be a new contract worth £100,000 a week, but he also stated Liverpool were "certainly not a club that is going to give way, way above what a player is worth at a certain time in their career." However, on 20 March, Rodgers said Sterling's contract situation would not be resolved until the summer at least.
On 12 July 2015, a deal was agreed for his transfer to Manchester City for an initial £44 million, with a further potential £5 million in add-ons, subject to personal terms and a medical, which would make him the most expensive English player of all time. On 14 July, Sterling officially joined Manchester City, signing a five-year contract. His debut came on 10 August, starting as City began the season with a 0–3 win away to West Bromwich Albion. Nineteen days later, Sterling scored his first competitive goal for Manchester City in a 2–0 defeat of Watford at the City of Manchester Stadium. Sterling scored his first career hat-trick as City beat Bournemouth 5–1 on 17 October.
On 27 March 2015, Sterling scored his first senior goal for England in a 4–0 UEFA Euro 2016 qualifier against Lithuania at Wembley Stadium. On 9 October 2015, Sterling scored his second goal of the qualifying campaign in a 2–0 victory against Estonia, by which point the team were already qualified. He was one of 23 players chosen for the final tournament.
In April 2015, Sterling was photographed by the Sunday Mirror allegedly smoking a shisha pipe, and by The Sun allegedly inhaling nitrous oxide for recreational purposes. Manager Brendan Rodgers said, "I don't think it is something you should be doing, it's as simple as that...Young players make mistakes. As long as they learn from them, that is what is important."