Driver was born in Saddleworth, Oldham, Greater Manchester, but moved to Gullane, East Lothian at the age of eleven. He began playing for Hutchison Vale AFC in Edinburgh, from where he joined the Hearts youth academy.
He first made his mark on Hearts' first team during a pre-season tour of Austria in 2006, where he started all three friendlies, creating four goals in the process with his direct play and crossing ability. In August 2006 Driver signed a five-year extension to his contract with Hearts, committing him to the club until 2011. He made his home debut in the league on 26 August 2006 against Inverness Caledonian Thistle, coming on as a substitute with 15 minutes to go and scoring four minutes later. Driver also scored a free kick in a 3–1 victory over Celtic at Celtic Park on 29 April 2007. In July 2008 Driver signed an amended contract with the club for another five years committing himself to the club until 2013.
Driver was the subject of two bids totalling £500,000 from Championship club Burnley in the summer of 2008, which was rejected by Hearts. Coventry City too made a £1 million bid in the 2009 January transfer window, which was also rejected. On 6 July, the BBC reported that Burnley had opened signing talks with Hearts. Joop Munsterman the FC Twente CEO reported on RVT Oost that Hearts had turned down a £3m offer for Driver. In all five clubs enquired about his availability including Chelsea.
In his first appearance on his return from injury Driver made his European debut against Paks in the Europa League scoring the third goal in their 4–1 win. Despite being fit Driver only appeared in seven of the first 20 competitive appearances under new manager Paulo Sérgio and a loan deal was considered, but did not come to fruition as Hearts were seeking a fee for the loan.
On 16 December the press reported that Driver was due to hand in a transfer request as he no longer wished to play under new manager Paulo Sérgio. The following day he was included in the squad as a substitute to face Dunfermline but was dropped after confirming to Sergio that he did not wish to play under him. Despite this Driver was a 62nd-minute substitute against Motherwell the following weekend replacing David Templeton.
On 19 February 2013, Driver joined Houston Dynamo on loan until the end of the season with his contract at Hearts due to expire in June. He made his debut with the side during a CONCACAF Champions League tie with Mexican-side Santos Laguna on 5 March 2013.
Driver made his league debut on 17 March 2013 against FC Dallas, where he also scored in the 79th minute.
He won MLS "Man of the Match" honors after scoring the match-winner vs. LA Galaxy on 5 May 2013 in a regular season rematch of the prior two MLS Cup finals He then scored against D.C. United on 8 May 2013.
Rumours circulated that he was to rejoin old club Heart of Midlothian; however this did not happen and he went on trial at Yeovil Town. On 24 January 2014, it was confirmed that Driver has signed a new contract with Houston Dynamo.
On 25 November 2014, it was announced that Houston had declined the option on Driver's contract. On December 8, 2014, his MLS rights were traded by with a 2016 MLS SuperDraft fourth-round pick by Houston to D.C. United in exchange for Samuel Inkoom and Joe Willis.
On 11 March 2015, it was announced that Driver would join Aberdeen on a short term deal until the end of the season. On 14 May 2015, Aberdeen announced that Driver would not be offered a new deal and would leave the club at the end of his contract.
In July 2015, Driver signed a one-year deal with the Doetinchem club, who had returned to the Eredivisie following promotion in the 2014–15 season. He made his debut in a 3–0 away defeat against Excelsior Rotterdam. He signed a two-year extension with the club on 30 May 2016, even with the club on the verge of relegation to the Dutch second tier.
Driver was previously a Scotland schoolboy international, scoring a goal in a 2–1 Victory Shield defeat by England on 22 November 2002.
England U21 manager Stuart Pearce called the uncapped Driver up for a friendly match against Azerbaijan. He was then called up for the 2009 European Championships. He made his debut and only appearance at the tournament in the 1–1 draw against Germany on 22 June 2009 during the group stages.
He was thought to be eligible to play for the Scotland senior team because of the new residency ruling recently introduced. He was not called up by then-manager George Burley as Burley stated that it was Driver's choice to officially make himself available for selection. On 4 February 2010, Driver committed his international future to Scotland after face-to-face talks with Scotland manager Craig Levein. Only one week after opting to represent Scotland, the Scottish FA informed Driver he was not eligible to play for the national team, as he had not been schooled in Scotland for the requisite period of time. This rule was subsequently altered to allow Driver to play for Scotland, although he is yet to do so.
Driver holds a U.S. green card which qualifies him as a domestic player for MLS roster purposes.As of 26 July 2017
Scottish Premier League Young Player of the Month: September 2007
Scottish Cup 2012