The "Turn Up The Music" singer was arriving in Sydney, Australia - just as Rihanna was leaving.
The Talk That Talk pop star was down in Australia all week promoting her new movie Battleship, and Brown was touching down in Sydney to perform and promote his new album, Fortune.
If the former couple had bumped into each other, it could have been a pretty awkward moment considering that Karrueche took the trip with him. Let's just say she probably wouldn't have been in the mood to deal with Rihanna.
Chris Brown tweeted a picture of his girlfriend with the caption: "Drunk before flight!!!!"
We'll never know what might have happened if these three ran into each other - this time. Check out the pictures of the trio as they stroll through the airport in Sydney.