DiCaprio, 39, kept things casual with a white T-shirt, denim jeans and a Boston baseball cap, while Garrn, 22, wore blue sweat pants and a dark T-shirt for a night on the courts on Saturday in New York City, reported E! Online.
"It was quiet there and no one was around. "Leo was encouraging to Toni on her tennis skills by using encouraging words, such as 'Good one, baby,'" an eyewitness said.
Garrn was apparently loving all the attention from her man as 'she was all smiles and focused on the match'.