Wimbledon 2023 Results: Instant Reactions to Monday's Winners and Losers

Eighth day action at Wimbledon concluded Monday, with four men and four women advancing out of the Round of 16 to the quarterfinals beginning Tuesday.

Not only did Monday feature appointment viewing, featuring three top-five players on the men's side, including No. 1 Carlos Alcaraz, and two top-three women, but it also delivered a stunning upset and controversial officiating.

All of Monday's matches saw the higher-ranked player advance, save for one. That, of course, was American Christopher Eubanks' shocking upset over No 5 Stefanos Tsitsipas in five sets.

In the match of the day between Alcaraz, the world No. 1, and Matteo Berrettini, who reached the Wimbledon finals two years ago, Alcaraz hung on to advance to his first Wimbledon quarterfinal.

Sixteen-year-old phenom Mirra Andreeva has captivated the world with her rapid ascent in women's tennis, but she exited the tournament in controversial circumstances on Monday.

Read on find a recap of all Monday's results, as well as reactions to some of the biggest storylines to emerge from the conclusion of Round of 16 play.

Monday Results

SEBASTIEN BOZON/AFP via Getty Images

TOPSHOT - Belarus's Aryna Sabalenka celebrates winning a point against Russia's Ekaterina Alexandrova during their women's singles tennis match on the eighth day of the 2023 Wimbledon Championships at The All England Tennis Club in Wimbledon, southwest London, on July 10, 2023. (Photo by SEBASTIEN BOZON / AFP) / RESTRICTED TO EDITORIAL USE (Photo by SEBASTIEN BOZON/AFP via Getty Images)

Men's Singles

No. 1 Carlos Alcaraz def. Matteo Berrettini, 3-6, 6-3, 6-3, 6-3

No. 6 Holger Rune def. No. 21 Grigor Dimitrov, 3-6, 7-6 (6), 7-6 (4), 6-3

No. 3 Daniil Medvedev def. Jiri Lehecka, 6-4, 6-2 ret.

Christopher Eubanks def. No 5 Stefanos Tsitsipas, 3-6, 7-6 (4), 3-6, 6-4, 6-4

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Women's Singles

No. 6 Ons Jabeur def. No. 9 Petra Kvitova, 6-0, 6-3

No. 3 Elena Rybakina def. No. 13 Beatriz Haddad Maia, 4-1 ret.

No. 25 Madison Keys def. Mirra Andreeva, 3-6, 7-6 (4), 6-2

No. 2 Aryna Sabalenka def. No. 21 Ekaterina Alexandrova, 6-4, 6-0

Christopher Eubanks Extends Improbable Run, Upsets Stefanos Tsitsipas

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LONDON, ENGLAND - JULY 10: Christopher Eubanks (USA) celebrates during his Gentlemen's Singles Round of 16 match against Stefanos Tsitsipas (GRC) during day eight of The Championships Wimbledon 2023 at All England Lawn Tennis and Croquet Club on July 10, 2023 in London, England. (Photo by Charlotte Wilson/Offside/Offside via Getty Images)

Not since Pete Sampras in 2000 has an American man won at Wimbledon.

But this year, that outcome is still in play...from an improbable source.

In just his ninth career appearance in a major, Atlanta, Georgia, native Christopher Eubanks continued a red-hot run at Wimbledon Monday, defeating world No. 5 Stefanos Tsitsipas of Greece—his first top-five win—3-6, 7-6(4), 3-6, 6-4, 6-4.

The 27-year-old now advances to his first major quarterfinal, where he will face No. 3 Daniil Medvedev. Eubanks' previous high-water marks were reaching the second round of the 2022 US Open and this year's Australian Open.

According to ESPN Stats & Info, Eubanks is the first Black American man to reach the Wimbledon quarterfinals since the start of the Open Era in 1968.

In his post-match interview, Eubanks said that over the years, he's had a "strenuous" relationship with grass surfaces. Earlier this year, however, he won his first ATP Tour title at the grass court event in Mallorca, and as his play at Wimbledon has shown, he may be turning over a new leaf on a previously challenging surface.

Mirra Andreeva Falls to Madison Keys in Controversial Fashion

Charlotte Wilson/Offside/Offside via Getty Images

LONDON, ENGLAND - JULY 10: Mirra Andreeva speaks to the umpire after throwing her racket to the ground during her Ladies Singles round of 16 match against Madison Keys (USA) during day eight of The Championships Wimbledon 2023 at All England Lawn Tennis and Croquet Club on July 10, 2023 in London, England. (Photo by Charlotte Wilson/Offside/Offside via Getty Images)

Russian teenager Mirra Andreeva (who is currently competing under a neutral flag amid the Russian invasion of Ukraine) is a fast-rising star in women's tennis, making it to the Wimbledon Round of 16 in just her second grand slam.

The dream-come-true circumstances of Andreeva's 2023 Wimbledon run, however, made her exit on Monday, losing to American Madison Keys in three sets, all the more unfortunate.

In her second set against Keys, Andreeva was issued a warning for throwing her racket in frustration. Then, serving at 2-5 down in the third set, Andreeva lost her footing and appeared to throw her racket down on the grass as she steadied herself. Umpire Louise Azemar Engzell docked Andreeva a point for unsportsmanlike conduct, and Keys converted the subsequent match point to advance to the quarterfinals.

Andreeva disputed the fact that she threw her racket down the second time, telling Engzell, "No, it's the wrong decision. Do you understand what you are doing? I didn't throw the racket, I slid." She then left the court without shaking Engzell's hand.

At only 16 years old, Andreeva has plenty of WTA tennis ahead of her, and continuing to improve in ability and maturity (she also hit a ball into the crowd in frustration at last month's French Open) will undoubtedly see her accomplish what she is capable of.