After just two seasons in the South African Premiership with Ajax Cape Town, an 18-year-old Pienaar was snapped up by parent-club Ajax Amsterdam in 2001.
In his five-year stay with the Eredivisie giants, the diminutive midfielder developed into an integral part of Ronald Koeman's squad, alongside the likes of Zlatan Ibrahimović, Maxwell, Cristian Chivu, Nigel de Jong, Rafael van der Vaart and Wesley Sneijder.
Despite being a part of a golden generation packed with talent, the Westbury-born playmaker stood out as one of the most highly-rated young talents in Europe.
After securing six major honours at the Amsterdam ArenA the precocious talent ventured to the German Bundesliga with Borussia Dortmund on a free transfer, replacing Arsenal-bound Tomas Rosicky.
While his stay with BVB was less fruitful in terms of silverware and individual honours with the struggling Die Borussen side, he was part of a squad that included club legend Sebastian Kehl and 2002 World Cup finalist Christoph Metzelder.
After just one season at the Westfalenstadion, a season-long loan deal to Premier League outfit Everton followed in the 2007 and the South Africa international went on to spend a decade in the English top-flight with the Toffees, Tottenham Hotspur and later Sunderland.
His time on Merseyside saw Pienaar form a brilliant partnership with Leighton Baines and play alongside Premier League stars such as Louis Saha, Tim Cahill, Mikel Arteta, Marouane Fellaini and Samuel Eto'o.
And between earning his cult-hero status an ill-fated stint with Tottenham allowed the soft-spoken South African legend to share a dressing room with now Real Madrid stars Luka Modrić, Gareth Bale and his former Ajax teammate Van der Vaart again.