Entertainment Sports Russell Wilson and Ciara Enjoy Date Night at Serena Williams' Box in the US Open On Thursday, Russell Wilson signed a mega five-year, $245 million extension with the Broncos By Giovana Gelhoren Giovana Gelhoren Instagram Digital News Writer People Editorial Guidelines Published on September 3, 2022 12:51 PM Share Tweet Pin Email Photo: Elsa/Getty Russell Wilson and Ciara enjoyed a date night Friday as they watched Serena Williams play her historic third singles match in the US Open. The couple looked cool and chic in matching outfits. The "One, Two Step" singer, 36, wore a white button-down dress with shades while the Denver Broncos quarterback, 33, wore similar shades, a maroon polo shirt and white pants. Russell Wilson Runs Football Drill with Son Future and Friend: 'Young Legends' There to support tennis icon Williams, 40, in what probably was her last tournament in a storied career, the couple watched as she was defeated by Ajla Tomljanović of Australia. JASON SZENES/EPA-EFE/Shutterstock Hopes were high in Arthur Ashe Stadium after Williams dominated early in the first two sets, but her talented opponent reeled her back in each time. Tomljanović won the first set 7-5 and Williams eked out a tiebreak win in the second, but couldn't overcome the Aussie in the third, losing 6-1. Serena Williams Likely Plays Final Match of Legendary Career After Losing at US Open: 'Most Incredible Ride' Williams said ahead of the tournament that she would be "evolving away from tennis" after the US Open, and expectations were that this would be her last time playing as a pro. The pair, who sat next to Williams' husband Alexis Ohanian — who wore an adorable shirt with their daughter Olympia's face on it — were not the only celebs in the stands. Bella Hadid, Spike Lee, Billie Jean King, Gayle King, Robert Kraft, Saquon Barkley, P. K. Subban and Ben Simmons all cheered for Williams in her third-round game. L: Caption . PHOTO: Al Bello/Getty C: Caption . PHOTO: Elsa/Getty R: Caption . PHOTO: Elsa/Getty Serena Williams Thanks Sister Venus After Final Match: 'Wouldn't Be Serena If There Wasn't Venus' As for Wilson, the superstar QB on Thursday signed a mega five-year, $245 million extension to the Broncos that includes $165 million in guaranteed money, the third most lucrative in terms of guaranteed money in NFL history, according to ESPN. Wilson shared moments from the special day on Instagram, showing his wife and daughter Sienna Princess, 5, and sons Win, 2, and Future Zahir, 8 — whom Ciara shares with rapper Future — at his side. "There's No Body like You God! There will NEVER be!" he captioned the Instagram carousel, which showed the family posing with team executives. Other photos show the kids playing in the press conference area, with Wilson pretending to interview Future. Russell Wilson Says His and Ciara's Three Kids 'Know How to Love': 'No Greater Feeling' The couple began dating in early 2015 and married a little over a year later in July 2016. Speaking with PEOPLE in July, Ciara talked about her kids' excitement about a new city. "So far, Denver's been incredible," the mom of three said at the time. Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. "They've been doing good," Ciara said. "When we told them the news, everything was like, 'Yeah! New team. Yeah! New school. Yeah!' I don't know if they really realize what's going on sometimes. They're excited about the new chapter."