Crystal Palace Bostock began his career with
Crystal Palace at the age of five. He also became the youngest ever Palace player to start a game, aged 15 years and 295 days, on 6 November 2007 against
Cardiff City at
Ninian Park.
Tottenham Hotspur in 2009 On 30 May 2008,
Tottenham Hotspur announced the signing of Bostock on their club website. Crystal Palace later issued a statement denying reports that an agreement had been reached with Tottenham. Tottenham and Crystal Palace entered negotiations over the transfer fee, but agreement could not be reached, leading to the sum being decided at a tribunal. On 9 July, the tribunal declared that Tottenham would pay £700,000 for Bostock, with add-on payments of up to £1.25m dependent on appearances and a further £200,000 should he make his full international debut. A sell-on clause entitled Crystal Palace to 15% of any profit Tottenham makes from any future sale of Bostock's contract. Crystal Palace chairman
Simon Jordan said he was so disgusted with Bostock and his stepfather that he intended to revoke and refund their Selhurst Park season tickets for 2008–09, which the pair had already purchased. Bostock made his first team debut for Spurs in an 8–0 pre-season win over Spanish side
Tavernes, providing the cross for
Aaron Lennon's opening goal. On 6 November 2008, he made his competitive match debut in the
2008 UEFA Cup game against
Dinamo Zagreb, coming on as a substitute, and becoming the youngest player ever to play for Spurs at 16 years, 295 days, just beating the previous record-holder
Ally Dick by six days. Bostock made a further two appearances in the UEFA Cup that season,
Loan spells On 13 November 2009, Bostock joined
League One club
Brentford on loan for a month, he was handed the number 17 shirt immediately. Bostock scored twice on his debut against Millwall. On 6 August 2010, Bostock had joined newly relegated
Hull City on a season-long loan. He scored with a 30-yard strike described as a "wonder goal" on his debut against Swansea on 7 August. On 31 December 2010, Tottenham Hotspur announced that Bostock had returned early from his largely unsuccessful loan spell at Hull City. Bostock joined
Sheffield Wednesday on loan on 30 January 2012 for the remainder of the 2011–12 season. He made his debut the following day as a substitute in a 1–1 draw with
MK Dons. He was recalled to Spurs in March after playing only four games. Bostock joined
Swindon Town on loan on 22 March 2012 for the remainder of the season, after Tottenham manager
Harry Redknapp said it would be good for him to play under
Paolo Di Canio. He made his debut on 25 March in the
2012 Football League Trophy Final, which Swindon lost 2–0 to
Chesterfield. He made his league debut against
Gillingham on 21 April. He made his home debut on 28 April, in a 5–0 win against
Port Vale in a game that saw Swindon crowned
League Two champions. He made his final appearance on the final day of the season in a 0–0 draw against
Bradford. He returned on loan to Swindon on 30 August 2012 until January 2013. He made his first appearance 2 days later against
Preston. He made his home debut on 5 September in the
Football League Trophy against rivals
Oxford United. Bostock returned to Tottenham on 7 January 2013. In February 2013, it was reported that Bostock was having trials with two different MLS clubs with a view to a loan move. He officially joined
Toronto FC on 8 March, and made his debut for team the following day in a 2–1 home victory over
Sporting Kansas City where he was substituted in the 85th minute. On 24 May, Bostock was given a waiver (release) by Toronto, ending his loan stint with the club. On 7 June, the
Premier League confirmed that Bostock was one of a number of Premier League players who were being released by their clubs and were now free agents, advertising their availability to other clubs. The official announcement from Tottenham was made on 10 June, which included Bostock, amongst a number of Spurs players who would not be re-signed and were being released.
Royal Antwerp On 11 July 2013, Bostock joined
Royal Antwerp in the Belgian second division under the tutelage of manager
Jimmy Floyd Hasselbaink. Despite scoring just one goal he flourished at Antwerp providing 16 assists in his first season and soon became a fans favourite helping the team to finish 6th in the league narrowly missing out on the playoffs.
OH Leuven His strong performances earned him a move to newly relegated side
Oud-Heverlee Leuven, where he continued to blossom. In his second season in Belgium, Bostock went on to help his new side OHL win promotion via the playoffs. Along the way he scooped the Proximus Player of the Season Award after scoring 13 goals and providing 19 assists.
Lens On 5 July 2016, Bostock joined
Ligue 2 team
RC Lens on a two-year deal. On 9 August 2016, Bostock scored his first goal for Lens with a 26th-minute free-kick against AC Ajaccio in the first round of the
Coupe de la Ligue. He scored his first league goal for the club in a 2–0 win over Nîmes on 15 August 2016. He scored an eighth-minute penalty in a 1–1 draw with
Troyes on 26 August 2016 before scoring twice in a 4–2 win over
Orléans on 20 September 2016. He scored his fifth league goal of the season with a penalty against
Red Star on 30 September 2016. Bostock was named Ligue 2 player of the month in September and then again in October 2016. He was awarded
Ligue 2 player of the year after his first season in French football on 15 May 2017.
Bursaspor In January 2018, Bostock signed with
Süper Lig side
Bursaspor, having agreed a -year contract with the club.
Toulouse In July 2018, Bostock returned to France signing a three-year contract with
Toulouse FC, managed by his former Lens boss
Alain Casanova. On 8 August 2019, Bostock returned to England with a season-long loan to Championship side
Nottingham Forest. He left Toulouse by mutual consent in October 2020.
Doncaster Rovers Bostock joined
League One club
Doncaster Rovers on an 18-month contract in January 2021. On 1 June 2022, following Doncaster Rovers's relegation from League One, it was announced that he had turned down a new contract and would be leaving the club. He made 39 league appearances for the club. In the
2023 National League play-off final, Bostock scored an 87th-minute equaliser against
Chesterfield to send the match to extra time. In the penalty shootout, Bostock attempted a
Panenka penalty but hit the bar. However, Notts County would prevail 4–3 to earn promotion.
Solihull Moors On 27 July 2024, it was announced that Bostock signed for National League side
Solihull Moors. He signed a two-year deal. He left the club in July 2025. ==International career==