Novak Djokovic can make Wimbledon history in his quarter-final against Flavio Cobolli, while his title rival Jannik Sinner must banish fears over an elbow injury when he faces Ben Shelton on Wednesday.
Djokovic, the seven-time champion, and world No 1 Sinner will book a blockbuster semi-final showdown if they win their last eight matches.
But before that heavyweight showdown is secured, both Djokovic and Sinner have pressing issues to resolve.
Djokovic will pass Roger Federer to take sole ownership of the all-time record for most Wimbledon men's semi-final appearances if he advances to the last four for the 14th time.
The Serb is bidding to become the second man in the Open era to reach the Wimbledon semi-finals aged 38 or older after Ken Rosewall, who made that stage aged 39 in 1974.
The 24-time Grand Slam champion is also aiming to reach a record extending 52nd major semi-final.
That would take him within two wins of breaking his tie with Margaret Court for the most Grand Slam singles titles by a man or woman.
Success at Wimbledon has been child's play for Djokovic, who has reached the final in every one of his appearances since 2018.
But it was a new experience for the sixth seed to watch his son Stefan take to the court against his quarter-final opponent this week.
Cobolli and Djokovic are good friends, so the Serb was delighted to see the Italian 22nd seed practice with his 10-year-old.
"They hit a few days ago. They played some points.Obviously, he loves tennis. He has everyone's signature, except mine. But that's okay, I'll accept that! Djokovic said.
"I'll have a conversation with my son and see what he has noticed in the game of Cobolli."
SINNER CONCERN
Sinner sparked fears he may have to pull out of the tournament after injuring his right elbow in an awkward fall during his fourth-round tie against Grigor Dimitrov.
The Italian top seed was trailing by two sets and on the brink of a shock defeat when Dimitrov pulled a pectoral muscle while serving and had to retire from the match.
Sinner subsequently cancelled a scheduled practice session at the All England Club on Tuesday after undergoing an MRI scan on the injury.
He is due to face American 10th seed Shelton later on Wednesday, when all eyes will be on the three-time Grand Slam champion's fitness.
The 23-year-old beat Shelton in straight-sets in the Wimbledon fourth round last year and also eliminated him in this year's Australian Open semi-finals.
Sinner, who has never made the Wimbledon final, is bidding to make history by becoming the first Italian player to reach the last four at the All England Club multiple times.
Shelton, eyeing a third Grand Slam semi-final at just 22, has already surpassed dad and coach Bryan, who reached the Wimbledon last 16 here 31 years ago.
In the women's tournament, Mirra Andreeva is the youngest Wimbledon women's quarter-finalist since 2007.
Under the wing of former Wimbledon winner Conchita Martinez, the Russian seventh seed has breezed impressively through the first four rounds without dropping a set.
But Andreeva faces former Olympic champion Belinda Bencic, who is enjoying her best ever Wimbledon just over a year after giving birth.
"I'm fighting with everything I have on the court, I still want to win very badly but it's much different now," Bencic said.
A five-time Grand Slam champion, Iga Swiatek has conquered her demons on the grass by reaching her second Wimbledon quarter-final on the back of her first final on the surface at Bad Homburg.
Her last eight opponent, Russian world number 19 Liudmila Samsonova, has won two of her five WTA titles on grass.