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Born and raised in England, he plays internationally for Gibraltar, where his father was born. With two goals, until 2019, he was Gibraltar's joint all-time leading scorer since joining UEFA along with Lee Casciaro and Liam Walker.

In August 2016 Gosling was loaned to Cambridge United of League Two on a six-month loan. His loaned was ended prematurely in November 2016 after making seven appearances for the club. On 16 January 2017 it was announced that Gosling would again go out on loan, this time to Forest Green Rovers of the National League.

On 6 June 2017, it was announced that Gosling had joined Torquay United following his release from Rovers. He was released by Torquay at the end of the 2017–18 season.

After not featuring for Bristol Rovers since the 26 December fixture against Wimbledon, Gosling joined Newport County on 26 February 2016 on an initial one-month loan. He made his debut on 1 March versus Crawley Town and played a further five times before returning to help Rovers earn promotion to League One. He signed a new contract with the Gas on 20 June 2016.

He played 23 league games across the season, scoring three goals, the last being the opener in a 7–0 rout of Alfreton Town in the last game of the regular season on 25 April 2015, relegating the opponents. He helped Rovers seal an immediate return to The Football League with a play-off victory over Grimsby on 17 May.

On 13 March 2014, Gosling joined Conference North side Gloucester City on loan until the end of the season. He made his debut three days later in a 3–3 draw against Gainsborough Trinity. Gosling made twelve appearances and scored three times: against Brackley Town, Harrogate Town and A.F.C. Telford United.

On 17 May 2014, Gosling announced that he was leaving Exeter, though he was offered a new contract by the club.

After leaving Exeter City, it announced on 24 June 2014 that Gosling had signed for recently relegated Conference Premier side Bristol Rovers for the 2014–15 season. He made his debut on 9 August as the Pirates began the season with a goalless draw against Grimsby Town. On 16 September, he scored his first goal for the club, concluding a 3–1 win over Nuneaton Town at the Memorial Stadium. Eleven days later, he struck the only goal for a win at Southport.

In January 2014, it was confirmed that Gosling was eligible to play for Gibraltar in upcoming friendlies and their Euro 2016 qualifying campaign by national team coach Allen Bula, and was under consideration for his next squad. He was eventually called up to the squad for friendlies against Estonia and Malta on 26 May and 4 June 2014, respectively. Gosling made his international debut in the match against Estonia at the A. Le Coq Arena in Tallinn, starting the match and scoring the equaliser in the eventual 1–1 draw. The goal was Gibraltar's first away goal since joining UEFA. He became Gibraltar's outright top scorer of all time on 7 September 2015 when he scored their second competitive goal, a consolation at the end of an 8–1 away loss to Poland in UEFA Euro 2016 qualifying. With the goal, he also became the first Gibraltar player to score more than one goal at the international level.

He made his debut for Exeter on 12 January 2013, as a late substitute for Steve Tully in a 3–0 win over Southend United at St James Park. He scored his first goal for the club to complete a 3–0 home win over Northampton Town in League Two on 2 March. After the match, Gosling said he hoped to become a first team regular at the club.

Born in Oxford, Gosling signed for Swindon Town Centre of Excellence as a ten-year-old. A year later he signed for Plymouth Argyle Centre of Excellence after he moved with his family to Newquay in Cornwall. He was released by Argyle at the age of 16 whereupon he enrolled at Hartpury College. He graduated through the Exeter City youth team to sign professional terms under Paul Tisdale in April 2012.

Jake Gosling (born 11 August 1993) is a footballer who plays as a winger who is currently unattached after leaving Torquay United in July 2018.