Carlos Alcaraz must put his friendship with Frances Tiafoe to one side as the defending champion targets a place in the Wimbledon last 16 on Friday.
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US Open champion Coco Gauff tackles British outsider Sonay Kartal in a collision of two different tennis worlds.
AFP Sport looks at three matches to watch on day five at the All England Club:
ALCARAZ AND TIAFOE IN FRIENDLY FIRE
Carlos Alcaraz says he will view fellow crowd-pleaser Frances Tiafoe as the enemy when the close friends clash for a place in the second week.
"Once you step on the court, players are not friends. You have to be on your own, focus on yourself, and try to beat him. That's how tennis works," said Alcaraz, who is bidding to become only the sixth man to win the French Open and Wimbledon back-to-back.
The Spanish star defeated Tiafoe in a five-set classic in the US Open semifinals in 2022 on his way to his first Grand Slam title.
"Frances, a great player, a great person as well. He always smiles. He always seems like he's enjoying his time on the court, off the court as well," added third seed Alcaraz in admiration.
"It's going to be a really fun match to play, to watch."
Tiafoe, the world number 29, is in the Wimbledon third round for a fourth successive year.
He needed five sets to see off Italy's Matteo Arnaldi in the first round before cruising past Borna Coric.
With two wins under his belt at the All England Club, it is the first time the 26-year-old has put together consecutive victories at tour level since April.
WORLDS COLLIDE FOR GAUFF AND KARTAL
US Open champion and world No 2 Coco Gauff takes on British qualifier Sonay Kartal, who has defied her humble ranking of 298 to reach the third round of a Slam for the first time.
The players inhabit different worlds on the tennis tour.
When Gauff was starting her US Open title push in August last year, Kartal was picking up just $550 for losing in low-level ITF event in Prague.
Gauff has already banked over $2.6 million this year from prize money.
Kartal arrived at the All England Club with just over $18 500 from her efforts on court but her progress to the last 32 at Wimbledon guarantees her a windfall of more than $182 000.
"I've got a couple of birthdays coming up with the family. I think they're a little bit happy that I won today," said the 22-year-old when asked how she intended to spend her money.
Gauff has been in impressive form this week, dropping just six games in two matches
MONFILS + DIMITROV = 70
With a combined age of 70, two of the sport's great entertainers meet for a place in the last 16.
Monfils, the 37-year-old dazzling and unorthodox Frenchman, made his All England Club debut in 2005 while Dimitrov made his bow four years later.
Surprisingly for players of such longevity, the two have only met five times, with Monfils holding a 4-1 advantage, including winning the pair's two Grand Slam meetings at the US Open, in 2011 and 2014.
Monfils made the last 16 at Wimbledon in 2018 while Dimitrov, 33, reached the semifinals 10 years ago, defeating Andy Murray in the last eight before losing to Novak Djokovic.
"I love the competition. I love the sport. I love the game. To be honest, it's a feeling that you can't have anywhere else," said Monfils when asked why he keeps playing.