Pienaar was born in Johannesburg.
He started his professional career at Ajax Cape Town, some 1,400 kilometres (870 mi) away from his hometown.
He was brought to the attention of Ajax CT whilst playing for the School of Excellence and was asked to join their youth academy.

Pienaar said, "I was very fortunate to go to the School of Excellence 2000, to be able to polish the technique and the talent that God gave me and to learn how to use it in the way that God had wanted me to." "
I was fortunate to work with the Dutch coach Leo van Veen, who helped me at Ajax Cape Town... He appreciated the way I played but at the same time he changed my mentality.
He taught me how to prepare for games, not just playing to please the crowd but also how to play for the team."

At Ajax Cape Town, he won the Rothman's Cup after beating Orlando Pirates 4–1 in the final on 13 December 2000, his final game for the club.
Pienaar was born in Johannesburg. He started his professional career at Ajax Cape Town, some 1,400 kilometres (870 mi) away from his hometown. He was brought to the attention of Ajax CT whilst playing for the School of Excellence and was asked to join their youth academy.
Pienaar said, "I was very fortunate to go to the School of Excellence 2000, to be able to polish the technique and the talent that God gave me and to learn how to use it in the way that God had wanted me to." "I was fortunate to work with the Dutch coach Leo van Veen, who helped me at Ajax Cape Town... He appreciated the way I played but at the same time he changed my mentality. He taught me how to prepare for games, not just playing to please the crowd but also how to play for the team."
At Ajax Cape Town, he won the Rothman's Cup after beating Orlando Pirates 4–1 in the final on 13 December 2000, his final game for the club.
Steven Pienaar