The Netherlands international playmaker left Real Madrid to join Tottenham under then-manager Harry Redknapp – a deal which many pundits and supporters alike lauded at the time considering his talent.
Van der Vaart went on to become a fans favourite at White Hart Lane, dazzling supporters with several top performances while grabbing a goal in the club’s only win at the Emirates Stadium to date.
But it could have been so different for the player, what with Dutch teammate Robin van Persie trying to broker a move to Arsenal rather than Tottenham.
“I had several conversations with Robin van Persie, my team-mate on the Dutch side, and he had spoken to Arsenal about me a few times, but I never heard anything," Van der Vaart told Fourfourtwo.
"I didn't regret it – joining Spurs was the best thing that happened to me.”
The 109-capped Dutch ace spent two seasons at Spurs before leaving the club for German outfit Hamburg, scoring an impressive 24 Premier League goals in 63 appearances.
His arrival coincided with Tottenham’s progression as a top four challenger in the Premier League and having arrived from Real Madrid, it was an indication of the club’s growing reputation as a big club.
Many Tottenham fans have fond memories of the player, and he has his own little piece of history at the club as being part of a first-team XI who recorded the club’s only win at the Gunners’ Emirates Stadium – a 3-2 win on 20 November 2010 as Spurs came back from 2-0 down at half-time.