When 34-year-old Pienaar joined Sunderland AFC at the beginning of the 2016/17 English Premier League campaign, he reunited with David Moyes, who worked with him extensively at their former club, Everton FC.
The former South Africa international arrived at the Tyne and Wear-based outfit as a free-agent after being released by the Toffees in July 2016. Pienaar brought some much-needed experience to the Sunderland squad after signing a one-year deal with the club following a successful trial stint.
However, the former Borussia Dortmund midfielder endured a disappointing campaign with the Black Cats, who were relegated to the English Championship for the first time in a decade at the end of the campaign.
Pienaar was one of the many Sunderland players, who suffered injury problems throughout the campaign and he could only make 17 appearances across all competitions and the Black Cats have decided against handing him a contract extension.
Nicknamed Schillo, Pienaar made 15 appearances in the Premier League - starting 10 matches in the process without scoring a single goal. He made 384 passes and 305 of them were successful.
Only one of his two shots at goal was on target, while creating seven goalscoring chances. Defensively, Pienaar won 55 duels and he made 19 tackles - conceding 16 fouls - winning four aerial duels in the process.
Pienaar's childhood club, Orlando Pirates expressed interest in his services prior to his move to Sunderland and the well-travelled midfielder had stated that he was open to returning home to join the Buccaneers after being released by Everton.
Nevertheless, Pirates went on to endure their worst season in the Premier Soccer League (PSL) era finishing 11th on the standings. A player of Pienaar's calibre would definitely add quality and some needed experience to the Bucs team as the Houghton-based side revamp their squad.
At the age of 35, Pienaar, who enjoyed a successful spell with Dutch giants Ajax Amsterdam, is on the wrong side of 30 and he is on his last leg. He has stated that he can still play competitive football for another season in his home country following a disappointing campaign in the English top flight.
Even if the Johannesburg-born player, who has been prone to injuries during his stay in England, doesn't play regularly at the Soweto giants, his influence and experience can rub off on the Pirates players - emulating his former Bafana Bafana teammate Benni McCarthy.
McCarthy joined the Buccaneers as a 33-year-old in 2011 after being released by Premier League side West Ham United FC. The accomplished striker took a promising striker Tokelo Rantie under his wing during his stint at Pirates.
Rantie, who went on to play in the Premier League for AFC Bournemouth, benefited from playing alongside the former FC Porto striker as they were instrumental as the Buccaneers remarkably secured three major trophies during the 2011/12 campaign.
One of Pienaar's teammates at Ajax Cape Town, Moeneeb Josephs recently revealed that Schillo remains a massive Bucs fan and alluded to the fact that his presence at the Soweto giants could turn things around for the team again.
WHERE WOULD PIENAAR FIT IN THE BUCS MIDFIELD?
The versatile midfielder was utilised both in the central midfield and the number 10 role by Scottish tactician Moyes last season, and the former Ajax Amsterdam midfield maestro proved that he remains a technically gifted player.If the Soweto giants do sign him, Pienaar, who was instrumental for Ajax as they won the 2000 Rothmans Cup - beating Bucs in the final, could provide an option in the middle of the park as we saw Pirates captain Oupa Manyisa blowing hot and cold in the midfield this past season.
Former Tottenham Hotspur and Borussia Dortmund midfielder Pienaar's introduction in the Pirates midfield could bring back some spark in the team. His experience, technique, and ability to link play would surely see him slot perfectly in the number 10 role.
There's no doubt that Pienaar has at least one good season left in him and it remains to be seen whether he will join Pirates or opt for Cape Town City, who have also expressed their interest in securing his services and bringing him back to the Mother City.