A controversial signing by Spurs caused upset as he became the second player (following Wayne Routledge) to travel to North London from Crystal Palace courtesy of a tribunal decision.
Attended the Nautical School in Blackfriars, South London.
Began his football career at Crystal Palace as a seven year old and developed into a talented young player, who was linked with Barcelona and Chelsea, who made a bid of £900,000 for him when he was 14, but the Eagles rejected it.
Bostock made his Crystal Palace debut at 15 years and 287 days old and he made two first team starts and three from the bench in season 2007-08. At the end of his contract at Selhurst Park in June 2008, he refused to sign a new contract with Palace, becoming disillusioned by the style of football being played there under Neil Warnock. He felt that a move to Tottenham would be the best one to develop his career. While Chairman Simon Jordan had put a price of £4.5 million on the young midfielder, Tottenham were asked to pay only £700,000 for Bostock when the fee was set by tribunal. This could rise to £1.25 million under certain conditions in the deal.
Became the youngest Spurs player ever when he entered the UEFA Cup group game against Croatian side Dinamo Zagreb on 6th November 2008, aged 16 years and 295 days and although he fared well, he failed to win a regular squad place, being loaned out to Brentford for a three month period during 2009-10, but he returned with some questions raised about his attitude at the club.
Selected for the England Under-19 squad that travelled to France in the summer of 2010 for the European Under-19 Championships, he played and scored a goal in the semi-final, but England lost out 1-3 to Spain. On his return, he hit the headlines with a blast that big money foreign players were stalling his progress in the game and this coupled with the issues around his loan the previous season could have seen him make an exit from the club, but his contract was extended to 2013 on the same day he went on loan to Hull City for a year.
On his return to Spurs, he went missing from the first team scene at the start of 2011-12, playing only a few Spurs XI matches, but re-emerged in a few squads and came on as a substitute against Cheltenham Town in the FA Cup, before almost immediately leaving on loan for Sheffield Wednesday. Bostock didn't stay at Hillsborough very long and was re-called, but then went on loan to Swindon Town until the end of the season, making a losing debut in the Johnstone's Trophy final at Wembley. The cash strapped club were unable to afford to keep him on loan, so he was sent back to Tottenham, but only long enough to pack a case for Canada, where he went off on loan to Toronto FC from March to May 2013. Shortly after his return to Spurs, he was placed on the released list issued on 7th June 2013.
John surprisingly signed for Royal Antwerp - a Second Division Belgian side, managed by former Leeds United and Middlesbrough striker Jimmy Floyd Hasselbaink. The midfielder seemed to thrive there, according to media reports, but at the end of the season it had been judged that he hadn't lived up to the Press, so he was on the move again, with a sideways move to RH Leuven in the summer of 2014.