Djokovic advanced to his 50th Grand Slam quarterfinal after beating No. 17 seed Cristian Garin of Chile 6-2, 6-4, 6-2. It is Djokovic's 12th quarterfinal berth at Wimbledon, tying him with Arthur Gore for third on the men's all-time list. He trails only Federer (18) and Jimmy Connors (14) on the list.
The 34-year-old Serbian is just the fifth player in the Open era (since 1968) to reach at least 50 Grand Slam quarterfinals, joining Federer (58), Chris Evert (54), Serena Williams (54) and Martina Navratilova (53), according to ESPN Stats & Information.
"It's a privilege to break records in the sport I truly love," said Djokovic, who won the tournament in 2018 and 2019. "I'm devoted to this sport as much as I think anybody out there on the tour. I just try to do my best."
Federer, meanwhile, became the oldest man to advance to the Wimbledon quarterfinals in the Open era with his 105th career win at the tournament Monday.
The 39-year-old Federer, who has won at Wimbledon eight times, defeated 23rd-seeded Lorenzo Sonego 7-5, 6-4, 6-2 on Centre Court to break the age record for quarterfinalists held by Ken Rosewall, who also was 39 when he reached the last eight in 1974.
"I guess to some extent it's nice to see that the work I put in paid off, that I'm able to play at this level," said Federer, who had only competed in eight matches this year before Wimbledon.
In other men's action, No. 16 seed Felix Auger-Aliassime of Canada upset fourth-seeded Alexander Zverev 6-4, 7-6 (6), 3-6, 3-6, 6-4 to earn his first berth in a major quarterfinal.
Fellow Canadian and No. 10 seed Denis Shapovalov also advanced to the quarters with a 6-1, 6-3, 7-5 win over eighth-seeded Roberto Bautista Agut, marking the first time two Canadian men have reached the quarterfinals of the same Grand Slam event.
No. 7 seed Matteo Berrettini, No. 25 Karen Khachanov and unseeded Marton Fucsovics were the other men to advance to the quarterfinals Monday.
The fourth-round match between second-seeded Daniil Medvedev and No. 14 Hubert Hurkacz was suspended in the fourth set until Tuesday because of inclement weather.
On the women's side, Cori "Coco" Gauff was eliminated in the fourth round again after losing to former Wimbledon champion Angelique Kerber 6-4, 6-4 Monday on Centre Court.
It is the second time Gauff has lost at that stage of the tournament, including her breakthrough run at the All England Club in 2019.
"I just feel like I'm close," Gauff said after the defeat. "... Always competitive in these matches against these top players, you know, like, making the second week, so I feel like I'm close.
"I just need to do better on certain points, and certain moments in the match I have to notice when the momentum changes and how to react to when it changes."
Top-ranked Ash Barty clinched a spot in the Wimbledon quarterfinals for the first time Monday after halting Barbora Krejcikova's 15-match winning streak. Barty beat the French Open winner 7-5, 6-3 in the fourth round.
Barty will next face Ajla Tomljanovic, who advanced when British teenager Emma Raducanu was forced to exit after a medical timeout in the second set.
Ons Jabeur, meanwhile, became the first Arab woman to reach the Wimbledon quarterfinals with her 5-7, 6-1, 6-1 victory over former French Open champion Iga Swiatek.
No. 2 seed Aryna Sabalenka, No. 8 Karolina Pliskova, No. 19 Karolina Muchova and unseeded Viktorija Golubic also advanced to the quarterfinals.