As a left-back with a tendency to play attacking football, Rose has been compared to Cyril Knowles, with particular focus placed on his speed, decision-making, and defensive abilities.

Rose started his professional career at Leeds United in 2006, having progressed through the club's youth ranks, but left for Tottenham Hotspur in July 2007 before making an appearance.

Following various loans to Watford, Peterborough United, Bristol City, and Sunderland, he established himself as a first-team player at Tottenham over the next six seasons, as well as starting in the 2019 UEFA Champions League final.

Following a loan to Newcastle United in 2020, he departed Tottenham in 2021, having made 214 appearances and scored ten goals for the club, and subsequently returned to Watford for a season.

[7] On 23 December 2020, Rose was arrested on suspicion of dangerous driving after his car reportedly collided with the central reservation on the A45 in Northampton.

[citation needed] Rose made his first start for Spurs in 2–2 FA Cup draw against his former club Leeds United in January 2010.

[19][20] On 7 May 2011, Rose started against Blackpool to fill in for regular left-back Benoît Assou-Ekotto, although playing out of his usual position, he was specifically praised by manager Harry Redknapp for his performance in the 1–1 draw.

[26] Watford manager Brendan Rodgers described Rose as a "highly talented, committed player" who possesses "good energy and real intelligence with the ball.

[34] Rose returned to Tottenham Hotspur in February 2011 after a series of minor injuries had limited his impact and appearances at Bristol City.

[38] Rose returned to Tottenham after being named the club's young player of the season to undergo surgery on a wrist injury in May 2013.

[39] On 22 August 2013 at the beginning of the season, Tottenham went away to Dinamo Tbilisi in Georgia where Rose scored in the play-off first leg which ended in a 5–0 win.

[40] Tottenham qualified for the group stage of the Europa League and in September, their first home match against Tromsø Rose suffered an injury.

[42] Rose missed the match where Tottenham suffered a 5–0 home defeat to Liverpool which subsequently saw André Villas-Boas dismissed as manager.

[47] In the 2014 summer transfer window Tottenham signed Ben Davies which would be competition in the left-back role as well as providing cover if Rose got injured.

[48] On 1 January 2015, Rose scored his first goal of the season in Tottenham's 5–3 Premier League victory over Chelsea at White Hart Lane.

[49] Rose scored again for Tottenham in the FA Cup third-round replay against Burnley at home, netting the final goal in a 4–2 victory.

[54] Rose was named as captain by manager Mauricio Pochettino for the first time in his career in a 2015–16 FA Cup match against Leicester City on 10 January 2016.

[72] On 30 January 2020, Rose moved clubs for the first time in seven years when he joined Newcastle United on loan for the rest of the season.

[81] On 1 June 2009, Rose was called into the England under-21 team for the European Championships taking place later in the month when striker Danny Welbeck was ruled out through injury.

[89] On 28 August 2014, Rose was named in the senior England squad for the first time, ahead of a friendly against Norway and a Euro 2016 qualifier against Switzerland in September, but did not feature.