Brown and Rihanna broke up in 2009, after he physically assaulted her on the night of the Grammy awards.
Since then, the pair seem to have reconciled, with Brown singing on two songs with the 'We Found Love' star, including a remix of her track 'Birthday Cake'. The collaborations have led to some division in Rihanna's fanbase, as some fans believe that she is setting a bad example by working with her former abuser.
However, a source close to the pair has told NewsAU that a surprise performance with the pair is a "definite possibility", though whether or not the two will perform together "won't be decided until the last minute".
According to reports, management for both Brown and Rihanna are eager to establish a professional partnership between the pair outside of the US.
Rumours of a rekindled romantic relationship between the two singers have been sparked in light of their recent musical collaborations. Rihanna has also recently been linked to Ashton Kutcher, after being spotted leaving his home at 4am.
Chris Brown will headline Supafest on April 14, alongside Rihanna, P.Diddy, Ice Cube, Lupe Fiasco, Missy Elliott, Ludacris, T-Pain and Trey Songz. The festival is also scheduled to play Melbourne and Perth.