Hugh Grant and Anna Wintour competed for the first day of the Laver Cup at the O2 Arena in London on Friday.
Editor-in-Chief of Vogue Anna, 72, showed off her signature sense of style as she wore a black dress with a pattern of red roses that cinched at the waist.
Actor Hugh, 62, opted for smart but casual attire, wearing navy blue trousers which he paired with a gray shirt, which he wore open at the collar.
He wore a navy blue jacket and a pair of brown suede shoes on his feet,
Journalist Anna wore a pair of high-heeled snakeskin boots and her famous black sunglasses.
She wore an eye-catching silver chain and happily posed at the event.
She sat next to Roger Federer’s father Robert Federer as his son played his farewell doubles match in the British capital.
Robert wore a gray jacket and shirt, which he left undone so the couple seemed to enjoy each other’s company.
They could be seen laughing and chatting as they sat side by side in the crowd.
Elsewhere, Bill and Melinda Gates were seen sitting next to each other at the venue.
Business magnate Bill, 66, wore a navy blue V-neck sweater and shirt and black baseball cap.
Melinda, 58, wore a black sweater and white shirt for her outing to the game.
JK Rowling remained focused as she watched day one of the Laver Cup at the O2 Arena in London on Friday.
The 57-year-old author sat in the crowd at the event where Roger Federer will play his farewell doubles match on Friday night.
Before taking her seat, she was seen in a black coat and mauve sweater as she posed with her husband Neil Murray, 51, next to the giant silver mug.
The Harry Potter author completed her look by wearing black trousers and matching boots.
Neil looked dapper in a black jacket and blue shirt, which he wore open at the collar.
He completed his look by wearing a pair of blue jeans while sporting a pair of black leather boots.
The pair were joined at the event by model and racing driver Jodie Kidd, who sat behind them in the crowd.
The 43-year-old TV personality looked chic in a white dress with a red and blue Aztec print.
Her garment featured a plunging neckline and she completed her look by accessorizing with some delicate dangle earrings.
She wore lots of makeup to emphasize her pretty features and sat close to her fiancé, Joseph Bates.
Elsewhere, rugby player Chris Robshaw, 36, sat nearby chatting with a pal.
The England sportsman, who plays for the San Diego Legion in California, cut a casual figure in a brown jacket and blue t-shirt.