[3] Van Aanholt joined Chelsea's youth ranks in 2007, making his professional debut while on loan at Coventry City on 9 August 2009 in a 2–1 Football League Championship win over Ipswich Town.

[6] On 29 January 2010, Van Aanholt joined Newcastle United on a one-month loan deal after regular left back José Enrique suffered an injury.

[8] He made his debut in a 1–0 win over Sheffield United on 1 February 2011,[9] and suffered a torn muscle in his thigh at the end of the month after playing six games.

Nine days later, he signed for Dutch club Vitesse on loan until the end of the season, alongside fellow Chelsea teammates Tomáš Kalas and Ulises Dávila.

He made his first start of the 2013–14 season in a 1–1 first leg draw away at Petrolul Ploiești in the UEFA Europa League, a match in which he was booked in the 86th minute.

[19] On 25 July 2014, Van Aanholt left Chelsea and signed for Sunderland for an undisclosed fee, believed to be between £1.5–2 million, on a four-year contract.

[20] He made his competitive debut on 16 August as Sunderland began their Premier League campaign away to West Bromwich Albion, assisting Sebastian Larsson for the final goal of a 2–2 draw.

[21] On 3 November, as Sunderland won 3–1 at Crystal Palace; Van Aanholt set up the opening goal for Steven Fletcher, but was later stretchered off in the first-half with a shoulder injury and replaced by Wes Brown.

The result sealed Sunderland's Premier League safety, and relegated local rivals Newcastle United, along with Norwich City.

[28][non-primary source needed] On 13 August 2016, in the opening game of the season, Van Aanholt conceded an early penalty, as Sunderland fell to a 2–1 defeat at Manchester City.

[41][42] On 19 November 2013, Van Aanholt won his first senior cap for the Netherlands in a friendly match against Colombia, coming on in injury time for Memphis Depay in a 0–0 draw at the Amsterdam Arena.