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Orlando Pirates transfer rumours: Masilela, Witbooi, Derbyshire

Posted on July 22, 2026
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Orlando Pirates could have several exciting new midfield options next season. Here’s the latest from the new Betway Premiership champions.

Masilela went to Spain with Orlando Pirates

Pirates’ recent tour of Spain was an opportunity given to 22-year-old midfielder Simphiwe Masilela. Blessed with technical quality and the ability to play in several central midfield roles, Masilela has the potential to become a fan favourite and was spotted in the number 38 jersey. 20-year-old central defender Cristian Derbyshire and 18-year-old midfield maestro Mpho Padime were also on tour in the Iberian nation. Watch this space.

Is Witbooi next?

Diminutive in stature, Cape Town City star Emile Witbooi is far from the finished product. However, the 17-year-old is highly thought of in South Africa. City has placed a big price tag on his head, thought to be rising to R20 million, so Pirates will need to think long and hard about how they structure any potential deal for the attacking midfielder born in 2008.

Big-name exits from Orlando Pirates

New champions Orlando Pirates will be a new-look outfit next term after several high-profile departures, notably Relebohile Mofokeng. The following players have left the club:

  • Thabiso Sesane
  • Selaelo Rasebotja 
  • Siyabonga Ndlozi 
  • Gomolemo Khoto 
  • Sonwabo Khumalo 
  • Blessing Ngiba
  • Seth Green 
  • Thabiso Lebitso 
  • Bandile Shandu
  • Sipho Mbule 
  • Tshegofatso Mabasa 
  • Relebohile Mofokeng

What’s next on the fixture schedule?

The Sea Robbers went down 3-2 to Al Ittihad on Tuesday. Next on their pre-season friendly schedule is a meeting with Las Palmas. Their first Betway Premiership fixture of the 2026-27 season is against Milford FC on Saturday, 1 August.

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