Pienaar made his UEFA Champions League debut while in the colours of Ajax Amsterdam and the furthest they went was the quarterfinals in the 2002/03 season.
They lost to Italian giants AC Milan in the last eight and the Italians went on to win the competition, beating rivals Juventus.
Benni McCarthy remains the only South African to have won the Champions League title, winning it with Portuguese outfit FC Porto in 2003/04.
"It’s the ultimate club competition. You can play in the Premier League or the Bundesliga, but this is the competition where you play against the best of the best from each country," Pienaar tells snl24.com/kickoff.
"Playing in it as a kid from Westbury was a dream come true. There’s a lot of unmissable moments. Being on the field and playing in the competition was unbelielable.
"At Ajax they won it in 1995 and it was the goal to win the trophy back. We went close when we got to the quarterfinals and we lost to AC Milan last minute.
"AC Milan actually went on to win the competition. As a player you dream of winning the trophy with the big ears.”
Currently there are no South African players campaigning in the Champions League.