number twenty-seven shirt ahead of the new season. Simpson made his Leyton Orient debut, coming on as a second-half substitute, in a 2–1 loss against Chesterfield. It wasn't until on 7 October 2014 when he scored his first goals in the second round of the Football League Trophy, in a 2–0 win over Dagenham & Redbridge. Four says later, on 11 October 2014, he scored his first league goal, in 2–2 draw against Sheffield United, followed up by scoring another two weeks later, in a 2–0 win over Doncaster Rovers. After scoring two goals throughout November, Simpson, however, was sidelined with injuries on two occasions that kept him out for the next three months. Simpson scored on his return from injury on 21 February 2015, in a 3–0 win over Oldham Athletic. Although he appeared out of first team around late-March and early-April, Simpson then returned to the first team and scored on 18 April 2015, in a 6–1 loss against Milton Keynes Dons. Although the club was relegated to League Two at the end of the season, Simpson finished his first season, making thirty-four appearances and scoring eight times in all competitions. In the 2015–16 season, Simpson started the season well in League Two when he scored the opening game of the season, in a 2–0 win over Barnet. He then scored three goals in three consecutive matches throughout August against Stevenage, Newport County and Bristol Rovers. After scoring two times throughout September, Simpson, again, scored five goals in four matches, including a brace against Crawley Town on 10 October 2015. By the end of 2015, Simpson scored nine goals in ten matches against York City (twice), Plymouth Argyle, Wimbledon, Mansfield Town, Portsmouth, Bristol Rovers and Stevenage (twice). As a result of his performance, Simpson was named the League Two Player of the Month for November. After scoring two goals by the end of January, Simpson went on a goal drought throughout February and didn't score again in a 2–2 draw against Carlisle United and scored a brace in a 3–2 win over Dagenham & Redbridge on 16 April 2016. A week later, however, Simpson was sidelined for a week, due to back injury. Up until this point, Simpson remained an ever-present player since the start of the season. At the end of the 2015–16 season, Simpson went on to make forty-eight appearances and scoring twenty-five goals in all