The Candy actress — who also shares Phineas, four, with her husband, Justin Timberlake — walked hand-in-hand with the little boy as they entered the stadium together.
Mother and son looked smart with Jessica donning a cream-colored suit and Silas wearing a striped polo shirt, long pants and sneakers.
Once inside, they sat alongside each other in the stands and watched the tennis together.
It's an ultra-rare appearance for Silas, as Jessica and Justin have kept their boys out of the spotlight over the years.
The family moved to Montana for a quieter life away from the limelight of Hollywood and have only given fans a sneak peek at their kids on social media, often obscuring their faces.
"I try to be conscious of making sure we can live a life where we're not weirdly private," Justin said during an appearance on Armchair Expert podcast in 2021.
"But we're conscious of making sure they can be kids for as long as possible and not have the weight of somebody else treating them differently because of something that their parents do."
Jessica adores motherhood, but admits it's not always easy.
"It's an amazing, amazing experience," she said on Today. "Incredibly hard — the hardest job in the world, and I've never been more thankful and grateful to my own mother."
In honor of Father's Day, Justin also opened up about the joy his kids bring him.
"My 2 greatest gifts. I learn more about myself every day just because you both chose me to be your Daddy," he began in his heartfelt social media post.
"I will always be there for you through your peaks and valleys… to lift you up and show you how high you can take this life and to pick you up when you fall. And, of course, to flood you with insufferable Dad-jokes all along the way."
"My knee-jerk reaction is 'Oh God, no. Please no,'" she said on Armchair Expert . "But then, I look at these kids and I'm like, 'Oh (expletive), they're probably going to be musical.' What are we going to do? Like, not let them play the piano? Or not let them take a voice lesson if that's their passion?"
She then said: "I don't want to be that parent to stifle a dream, but, man, if my kid would just be like, 'Let's go learn about corn in Iowa,' (I'd be like), 'Great.' I would so much rather them be an engineer or something."
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