competitions, finishing as the second's top-scorer behind Matty Taylor. For his performance, Simpson was named the fifth best player in League Two and League Two PFA Team of the Year. In addition, Simpson was named Away Player of the Year award at the 20th annual Supporters' Club Dinner-Dance. In the 2016–17 season, Simpson suffered a setback at the start of the season when he was sidelined with a sickness bug. While sidelined, Simpson was linked with a move away from the club, with Southend United keen on signing him, but the transfer move never happened. After returning to the first team, his return was short-lived when he suffered a back injury and was sidelined for weeks. After returning to the first team from injury, Simpson suffered a goal drought since the start of the season and it wasn't until on 12 November 2016 when he scored a brace, in a 3–0 win over Colchester United. He then scored again on 10 December 2016, in a 1–0 win over Accrington Stanley. By the first half of the season, Simpson went on to make seventeen appearances and score three times in all competitions. Philadelphia Union Simpson signed for Major League Soccer team Philadelphia Union on 9 January 2017. Reports suggested that Simpson's departure was due to him being unsettled at Orient. Upon joining Philadelphia, the club's sporting director Earnie Stewart, commented on his move, saying: "Jay brings goal scoring prowess to our team, in addition to a valuable veteran presence, as he has demonstrated with multiple clubs in England." Simpson started the first match of the 2017 season, against Vancouver Whitecaps, and scored the Union's first goal of the season against 2016 Eastern Conference Champions, Toronto FC. He was restricted to substitute appearances for most of his tenure at the club, starting five of his 30 appearances. His final start came against Sporting Kansas City in September 2018. The match also saw him score his second and third goals for the club. Simpson was released by Philadelphia on 19 November 2018. Return to Leyton Orient On 12 February 2019, it was announced that Simpson would rejoin Leyton Orient. He started his first competitive match in almost five months in a National League fixture against Maidenhead United on 16 February. Nea Salamina On 30 June 2019, it was announced, that Simpson had joined Cypriot club Nea Salamina on a 1-year contract. Welling United