The 35-year-old South African recently announced his retirement from the game, bringing an end to an 18-year career in which he was one of Africa's finest exports to the English Premier League.
In his two stints with the Toffees he was involved in 11 Merseyside Derbies, but only finished on the winning side once, thanks to a Dan Gosling goal in an FA Cup fourth round replay in 2009.
Pienaar admits it was the presence of Liverpool talisman Gerrard that compounded his misery, singling out the former England midfielder as the toughest nut to crack in a career that took him from South Africa to the Netherlands, Germany, and finally England.
When asked who his toughest opponent had been, Pienaar told KweséESPN: "Steven Gerrard... he actually got me sent off in the Derby, so I will say him!"
That red card came in a fierce Derby in February 2010 when, within 14 seconds of the start, he had been crunched by Liverpool defender Jamie Carragher to set the tone of the encounter.
Pienaar endured a running battle with Gerrard all game and after the Reds midfielder had committed another foul late on, Pienaar sought retribution and paid the price with a second yellow card.
"He was one of the toughest for me and he got stuck in as well. Some games he got right into me... the way he was playing he was the most difficult opponent to play against," 'Schillo' added.
But the fierceness of the contest aside, Pienaar was able to admire the contribution that Gerrard made, even if it came at a cost to his team.
"Playing against him in the Derby games was unbelievable. The way he played, the qualities he had on the pitch, driving a team ... he could turn a game on his own.
"Playing against him was hard, but even watching him from afar when Liverpool were playing games ... I was like, 'how does he do it?'"
Gerrard spent 17 years at Anfield and retired at the end of 2016, after a short spell with LA Galaxy in Major League Soccer.
He never won a League title with the Reds, but was a key player in one of the club's greatest nights when they came from 3-0 down at halftime to defeat AC Milan on penalties in the final of the UEFA Champions League in 2005.