It took a few weeks for the new Everton signing to earn his place in David Moyes' starting XI, but he announced himself properly to the Toffees faithful in his third Premier League start against Middlesbrough. The South African received a pass on the edge of the box and flicked it wide to Mikel Arteta before drifting into space to receive the ball back and diverting into the bottom corner to make it 2-0.
Once up and running on Merseyside, Pienaar became a standout in the Premier League for his cute skills, neat goals and dancing celebrations. His rhythmic style made him tricky for defenders to stop and a delight for fans to watch, while his smart movement off the ball allowed him to get into dangerous positions to create plenty of highlights in his long Premier League career.
"I liked Goodison Park, even though I always felt so nervous driving there that I played gospel music in my car... I had a good partnership with Leighton Baines on the left," he said years later. "We were two honest players on one side who worked hard for each other. We’d do the dirty work, the hard work."
After his first season at Goodison Park, he continued to develop into a proper fan favourite. He set up and scored winning goals against Bolton and Tottenham respectively in the 2008-09 campaign and masterminded a 2-0 win against Sunderland by netting one and assisting the other after earning a draw with another strike in a 3-3 draw with Aston Villa. He ended the campaign with three goals and seven assists, helping Everton to a second consecutive fifth-placed finish in the Premier League.
“Before I came to England I was a bit of a ‘lazy’ player," he said later. "I was at Ajax six years and just played in an attacking way, but once I got to Everton I had to change my work ethic, learn to track back, and it has made me a better player."
Eventually, it was clear Pienaar was worthy of a step up and there was plenty of interest further south. Chelsea were keen, but Tottenham came calling, too, and after some prayer and reflection, he joined Spurs for as little as £3 million in January 2011, teaming up with the likes of Luka Modric, Gareth Bale, William Gallas, Jermain Defoe and former Ajax team-mate Rafael van der Vaart in Harry Redknapp's team.
"It wasn't about the money, it was about ambition," he said. "We want to fight and to play every game at the highest level and play in the Champions League and that's what I want every season, and that's why I made the decision to join Spurs."
He added: "Looking from the outside, you can see the attacking football Spurs play, it is in a different class, making you sit on the edge of your seat. Everyone can see they are a club on the up, always fighting for a place in the top four and the Champions League... I asked a lot of people, and some were telling me to join Chelsea or go to Spain, but I prayed and followed my heart. Time will tell if it is the best decision, and if I fail, I will take the responsibility."
In hindsight, it was not the best decision. His time at White Hart Lane was a disaster as he made just 10 Premier League appearances and was loaned back to Everton just a year after his departure before returning on a permanent deal.
Some say that in football you should never go back, but it worked out well for the South African. He enjoyed his most prolific season in the Premier League in 2012-13, netting six goals and setting up six more - including a late equaliser as they beat Tottenham 2-1. A few weeks later, he got a goal and assist in a 2-1 win against West Ham and Everton finished sixth in the table.