Cincinnati Open 2026 Upsets: The Biggest Men’s and Women’s Failures So Far

The Cincinnati Open is only entering its second week, but the damage list already looks like something from a much later stage of the tournament.

Novak Djokovic is gone.

Ben Shelton is gone.

Jack Draper never reached the second round.

Stefanos Tsitsipas barely survived his opener before losing in straight sets to Felix Auger-Aliassime.

Casper Ruud left injured.

Jelena Ostapenko was dismantled in straight sets.

Barbora Krejcikova lost her first match.

Leylah Fernandez was beaten from a set up.

Daria Kasatkina exited in the opening round.

Venus Williams left Cincinnati with another defeat and an increasingly painful losing streak.

Not every early exit belongs in the same category. Some players entered injured. Others ran into excellent opponents. A few simply played badly. There is also a difference between a disappointing tournament and a disappointing season.

But Cincinnati matters because of where it sits on the calendar.

The US Open begins at the end of August, which means this tournament is one of the final opportunities for players to test their hard-court games against elite opposition before New York. For anyone carrying form, fitness or confidence problems, an early loss can feel much bigger than one failed Masters or WTA 1000 campaign.

That is especially true this year.

Carlos Alcaraz and Jannik Sinner did not even make it to the starting line because of injuries. That opened space in the men’s draw for players who might ordinarily face much tougher routes. Several failed to take advantage.

The women’s draw has been more stable at the very top so far, with Aryna Sabalenka, Iga Swiatek, Coco Gauff and Elena Rybakina still alive at the time of writing. The biggest disappointments have therefore come from the next tier of established names rather than the championship favorites.

So who have been Cincinnati’s biggest failures so far?

This ranking considers expectations entering the tournament, quality of defeat, opportunity lost, recent form and what the result means heading toward the US Open.

Official live draws and results are available through the ATP Tour’s Cincinnati Open results center and the WTA’s official Cincinnati scores page.

Cincinnati Open 2026 Biggest Disappointments at a Glance

Rank	Player	Exit	Why It Hurts
1	Novak Djokovic	Second round, lost to Thiago Agustin Tirante	Physical collapse in first match since Wimbledon before US Open record chase
2	Ben Shelton	Second round, lost to Jaime Faria	Arrived as back-to-back Canadian Open champion and lost in straight sets
3	Jack Draper	First round, lost to Martin Landaluce	Blew 5-2 second-set lead and six set points during fragile comeback
4	Jelena Ostapenko	Second round, lost to Magdalena Frech	Won only four games in a one-sided defeat
5	Stefanos Tsitsipas	Second round, lost to Felix Auger-Aliassime	Cincinnati has historically suited him, but slump continues
6	Barbora Krejcikova	Second round, lost to Sara Bejlek	Grand Slam champion beaten in straight sets in opening match
7	Leylah Fernandez	Second round, lost to Wang Xiyu	Seeded player surrendered control after winning first set
8	Daria Kasatkina	First round, lost to Zeynep Sonmez	Experienced seed failed to convert a favorable opening-round position
9	Grigor Dimitrov	First round, lost to Sebastian Baez	Wild-card comeback stalled after winning first set
10	Venus Williams	First round, lost to Emiliana Arango	Another heavy defeat extended losing streak to 14 matches

1. Novak Djokovic: The Biggest Failure Because the Stakes Were the Highest

The scoreboard says Thiago Agustin Tirante beat Novak Djokovic 2-6, 6-4, 6-4.

The real concern starts after the first set.

Djokovic looked comfortable early. Then the heat and humidity began to overwhelm him.

During an extraordinary 18-minute service game in the second set, the 39-year-old dropped to his knees and later required medical attention to cool down.

He attempted to manage his energy through the rest of the set, returned after a clothing change looking better in the decider, but cracked again at 4-4 with a string of errors.

Tirante served out the biggest victory of his career.

The defeat matters because Cincinnati was Djokovic’s first competitive appearance since his Wimbledon semifinal loss to Jannik Sinner.

He did not come to Ohio merely to collect another Masters title.

He needed match repetitions.

Instead, he received three sets and a physical warning.

The Sports Encounter examined the consequences in our analysis of what Djokovic’s Cincinnati fall means for the US Open.

One early loss does not remove a 24-time major champion from New York contention. Djokovic has repeatedly shown that he can reach Grand Slam semifinals and finals without conventional warm-up schedules.

But this was still Cincinnati’s biggest failure so far because the entire tournament was supposed to answer a specific question.

Could Djokovic build enough hard-court match fitness before trying to win Grand Slam No. 25?

Cincinnati supplied very little reassurance.

Why this ranks No. 1

The upset itself was huge. Tirante entered the match ranked No. 50 and had never beaten Djokovic.

The physical element made it more damaging.

Djokovic did not simply lose a tight match while playing well. He visibly struggled to sustain the level required by difficult conditions.

New York can be hot and humid too.

That does not make Cincinnati predictive.

It makes it relevant.

2. Ben Shelton: From Canadian Champion to Straight-Sets Exit

Ben Shelton may have suffered the most surprising form reversal of the men’s tournament.

He entered Cincinnati after winning the Canadian Open for the second consecutive year.

He had not dropped a set during that title run.

His serve was firing.

His confidence looked restored.

Then Jaime Faria beat him 6-4, 6-4.

Faria had never previously beaten a top-10 player.

He saved 11 of the 12 break points Shelton created and converted three of his own opportunities.

The timing makes this one sting.

Shelton had just re-established himself as one of the most dangerous North American hard-court players. The Sports Encounter covered that surge when Shelton defended his Canadian Open crown and joined rare Masters company.

Cincinnati offered a chance to turn one big week into a genuine summer run.

Instead, the momentum disappeared immediately.

This was a missed opportunity, not a crisis

Shelton’s situation is very different from Djokovic’s or Draper’s.

There is no obvious injury concern.

His recent form is excellent.

He has already banked significant confidence before the US Open.

That makes the defeat easier to recover from.

It also makes it harder to explain.

Faria played the pressure points better and repeatedly escaped from trouble on serve.

Shelton could not impose the kind of first-strike tennis that had carried him through Canada.

Sometimes a great week is followed by a flat one.

Cincinnati may simply be that.

3. Jack Draper: The Loss That Looked Like a Confidence Breakdown

Jack Draper did not lose to a random qualifier while playing terrible tennis for two hours.

His defeat was more painful because he had a route back into the match and could not finish it.

Martin Landaluce beat him 6-3, 7-5.

Draper led 5-2 in the second set.

He held six set points.

He converted none of them.

Landaluce won five consecutive games.

Match over.

The Sports Encounter covered the collapse in detail in our Cincinnati opening-day report and later examined the larger question in Can Jack Draper Turn It Around at US Open 2026?

Draper once reached world No. 4.

He reached the US Open semifinal in 2024.

Injuries have since wrecked his continuity.

An arm bone problem cut short his 2025 season. A knee issue disrupted 2026. He withdrew from Wimbledon and returned in Canada only to lose immediately to Terence Atmane.

Reuters reported him at No. 143 entering Cincinnati.

That context changes how we judge this defeat.

The expectation was not that Draper should win Cincinnati.

The expectation was that he should demonstrate progress.

Losing five straight games from 5-2 suggested the mental and competitive rhythm has not returned yet.

The US Open qualification issue makes everything heavier

Draper’s ranking collapse could force him through qualifying in New York.

That would be extraordinary considering he reached the semifinals there only two years ago.

This is why his Cincinnati exit belongs high on the list.

Every match currently matters more for Draper than it does for most established players.

4. Jelena Ostapenko: Four Games Won in an Alarmingly Flat Defeat

Not every major disappointment requires a famous opponent.

Sometimes the scoreline says enough.

Magdalena Frech beat No. 26 seed Jelena Ostapenko 6-1, 6-3.

Ostapenko won four games.

That is a poor outcome for a former Grand Slam champion at a WTA 1000 event less than two weeks before the US Open.

Frech deserves credit.

She controlled the match, absorbed Ostapenko’s power and refused to provide the Latvian with the rhythm she prefers.

Still, established players are judged partly by how competitive they remain when Plan A fails.

Ostapenko never found a meaningful Plan B.

The loss was Cincinnati’s clearest women’s underperformance so far because it combined seeding, experience and the sheer one-sidedness of the result.

5. Stefanos Tsitsipas: Tsitsinnati Lasted One More Match

The Cincinnati Open’s social media team had some fun after Stefanos Tsitsipas won his first-round match, creating the playful nickname “Tsitsinnati.”

It did not survive long.

Felix Auger-Aliassime beat him 6-3, 7-5 in the second round.

Tsitsipas’ Cincinnati history made this an especially important tournament.

He reached the final here in 2022 and has traditionally looked comfortable on the Ohio hard courts.

He also entered desperate for evidence that his broader decline could be reversed.

His ranking has fallen dramatically from his peak years.

He survived Valentin Royer in the opening round 7-6(4), 7-5, but Auger-Aliassime exposed the gap against a stronger opponent.

The defeat itself was not humiliating.

The absence of progress is the problem.

Cincinnati offered familiar surroundings, a favorable chance to rebuild confidence and another important checkpoint before New York.

Tsitsipas leaves without a signature win.

6. Barbora Krejcikova: A Grand Slam Champion Gone in Straight Sets

Barbora Krejcikova’s 7-6(5), 6-4 defeat to Sara Bejlek was one of the more significant women’s upsets of the second round.

Bejlek had already announced herself by destroying former world No. 1 Karolina Pliskova 6-0, 6-2.

So there was warning.

Krejcikova still should have expected to handle the match better.

The Czech is a multiple Grand Slam champion across singles and doubles and possesses far more experience in high-level tactical matches.

Instead, Bejlek took the first-set tiebreak and never allowed Krejcikova to settle into a recovery.

This is exactly the kind of loss that can become dangerous before a major.

The tennis was competitive.

The result was clean.

Krejcikova now leaves Ohio without building any momentum.

7. Leylah Fernandez: From Control to a Three-Set Exit

Leylah Fernandez’s defeat followed a familiar and frustrating pattern.

She won the opening set 6-3 against qualifier Wang Xiyu.

Then the match completely reversed.

Wang won the next two sets 6-2, 6-2.

The Chinese qualifier recorded only her second top-50 win of the season.

For Fernandez, seeded No. 30, the disappointment comes from the inability to control a match she had already put in her favor.

The Canadian remains one of the tour’s most dangerous competitors when rallies become emotional and physical.

She can make opponents uncomfortable.

But consistency has always separated her best tournament runs from ordinary weeks.

Cincinnati became another example.

8. Daria Kasatkina: A First-Round Exit After Being in Position to Advance

Zeynep Sonmez beating Daria Kasatkina 2-6, 7-6(4), 6-3 was one of the opening day’s most important WTA upsets.

Kasatkina won the opening set comfortably.

She then lost a second-set tiebreak and could not regain control in the third.

The Russian-born Australian has built her career around variation, defense and problem-solving rather than overwhelming power.

Those qualities normally make her difficult to eliminate early.

Sonmez found a way through.

The result earns a place on this list because Kasatkina had already established authority over the match and let it disappear.

9. Grigor Dimitrov: Another Comeback Stalls

Grigor Dimitrov entered Cincinnati on a wild card after injury problems had pushed his ranking down to No. 138.

That context deserves sympathy.

It does not make the defeat painless.

Dimitrov won the first set against Sebastian Baez 6-1.

Baez responded 6-3, 6-4.

The Bulgarian therefore joined Draper among the established players whose comeback campaigns ended before they could generate meaningful momentum.

Cincinnati was never primarily about a title for Dimitrov.

It was about testing whether his body and timing could sustain competitive tennis again.

One promising set followed by elimination gave only a partial answer.

10. Venus Williams: The Story Is Bigger Than Cincinnati

Calling Venus Williams a “failure” requires context.

At 46, simply continuing to compete at tour level is remarkable.

She has nothing left to prove historically.

Her Cincinnati result was still difficult.

Emiliana Arango beat her 6-2, 6-2.

The defeat extended Williams’ losing streak to 14 matches and left her winless in 11 appearances this season.

She entered on a wild card ranked outside the top 600.

Expectations therefore cannot reasonably resemble those placed on seeded players.

But results remain results.

Williams has now struggled to make these returns competitive against players who are far below the level of opponents she once dominated.

The emotional question is increasingly whether these appearances still provide what she wants from the sport.

That is hers to answer.

Casper Ruud Belongs in a Different Category

Casper Ruud technically exited early, but calling him one of Cincinnati’s biggest failures would be unfair.

He retired while trailing Christopher O’Connell after experiencing back discomfort.

That is an injury story rather than a performance collapse.

The concern is the US Open.

Ruud now needs his back to settle quickly enough to avoid another compromised major campaign.

The same distinction applies to players who never started the tournament.

Carlos Alcaraz and Jannik Sinner Failed to Make Cincinnati, But They Did Not Fail at Cincinnati

Two of the biggest men’s names are absent entirely.

Carlos Alcaraz withdrew because of the wrist injury that has already kept him out of Roland Garros and Wimbledon.

Jannik Sinner withdrew because of a right knee problem.

The Sports Encounter covered both situations in our Alcaraz injury analysis and Sinner Cincinnati withdrawal report.

They cannot be ranked among the tournament’s on-court failures because they never played.

Their absence did, however, increase the opportunity for everyone else.

That is part of why Shelton and Djokovic’s exits stand out so sharply.

Why the Women’s Top Four Have Avoided the Disaster List So Far

The women’s tournament has not suffered the same top-end collapse.

Aryna Sabalenka survived difficult conditions to beat Talia Gibson 6-2, 7-6(2).

Coco Gauff recovered from losing the first set 6-2 against Liudmila Samsonova and won 6-4, 6-1 in the next two.

Iga Swiatek initially struggled against Maria Sakkari before winning 12 of the final 14 games to advance 4-6, 6-1, 6-1.

Elena Rybakina was leading Magdalena Frech when play was ongoing at the time of this article’s preparation.

That difference matters.

The biggest women’s stars have experienced pressure without exiting.

The second tier has supplied most of the damage.

The Most Embarrassing Loss and the Most Damaging Loss Are Not the Same

If we judged only by scoreline, Ostapenko would have a strong argument for No. 1.

If we judged by blown opportunities, Draper might lead.

If we judged by momentum lost, Shelton would be difficult to beat.

Djokovic ranks first because of consequence.

He had one tournament between Wimbledon and the US Open to test himself under competitive conditions.

His first match produced both defeat and physical distress.

That creates questions extending far beyond Cincinnati.

Shelton’s loss is shocking but probably temporary.

Draper’s is part of a deeper crisis.

Those distinctions matter more than raw rankings.

Who Has Been the Biggest Men’s Failure?

Novak Djokovic.

He arrived as one of the headline attractions, had realistic title ambitions in a draw missing Sinner and Alcaraz, and needed hard-court preparation before attempting to win his 25th Grand Slam.

Instead, he lost his first match to No. 50 Tirante and struggled physically.

That is the most consequential men’s disappointment.

Who Has Been the Biggest Women’s Failure?

Jelena Ostapenko.

No top-four seed has crashed out yet, so the women’s ranking is less dramatic.

Among established seeded players, Ostapenko’s 6-1, 6-3 defeat to Frech was the weakest combination of scoreline and performance.

Krejcikova and Fernandez are close behind because of their reputations and how little momentum they take toward New York.

What These Cincinnati Failures Mean for the US Open

The US Open changes the interpretation of almost every result in Cincinnati.

If this were March, a Masters early exit could disappear within another tournament or two.

There is very little calendar left now.

Djokovic needs to decide how to replace the matches he expected to play in Ohio.

Draper may have to navigate qualifying.

Tsitsipas needs confidence without another obvious place to find it.

Krejcikova and Ostapenko head toward New York without a meaningful Cincinnati run.

Shelton has a better problem. His Canadian Open title means he can dismiss one bad match more easily than everyone else on this list.

The Sports Encounter’s US Open 2026 preview tracks the shifting fitness, form and title picture as New York approaches.

TSE Verdict: Cincinnati Has Exposed More Than Bad Tennis

The biggest failures at this tournament share very little.

Djokovic is fighting age, match rhythm and physical management.

Draper is trying to reconstruct a career interrupted by injuries.

Shelton arrived hot and simply ran into a player who executed better on the day.

Tsitsipas is searching for evidence that his decline has bottomed out.

Ostapenko produced a poor performance.

Krejcikova and Fernandez failed to turn experience into progress.

Williams is competing against time as much as any opponent.

That is why Cincinnati has been so revealing.

A tournament this close to a Grand Slam does not merely eliminate players.

It exposes where they are.

Some of these losses will disappear the moment New York begins.

Others may look like warnings we should have taken more seriously.

Djokovic’s heat struggle belongs in the second category until he proves otherwise.

Draper’s confidence problem may be even harder to solve.

Shelton has already shown enough this summer to believe Cincinnati was an interruption rather than a regression.

The women’s draw has so far protected its biggest stars, but the next round brings more direct collisions and therefore more opportunity for this list to change.

The Cincinnati Open still has nearly a week left.

Its disappointment column is already crowded.

For continuing match reports, upsets, analysis and US Open implications, follow The Sports Encounter’s Cincinnati Open coverage.

Frequently Asked Questions

Who is the biggest disappointment at the 2026 Cincinnati Open so far?

Novak Djokovic ranks as the biggest disappointment because he lost his first match to Thiago Agustin Tirante while visibly struggling with heat and physical issues. Cincinnati was his first competitive tournament since Wimbledon and an important US Open warm-up.

Who beat Novak Djokovic in Cincinnati?

Thiago Agustin Tirante defeated Djokovic 2-6, 6-4, 6-4 in the second round.

What happened to Ben Shelton?

Jaime Faria beat Shelton 6-4, 6-4 only days after the American won his second consecutive Canadian Open title.

Who eliminated Jack Draper?

Martin Landaluce defeated Draper 6-3, 7-5. Draper led 5-2 in the second set and held six set points before losing five consecutive games.

Who has been the biggest women’s disappointment?

Jelena Ostapenko has the strongest case so far after losing 6-1, 6-3 to Magdalena Frech. Barbora Krejcikova, Leylah Fernandez and Daria Kasatkina are also among the notable early exits.

Is Aryna Sabalenka still in the Cincinnati Open?

Yes. Sabalenka advanced through her opening match against Talia Gibson and remained in the tournament at the time of publication.

Is Iga Swiatek still playing in Cincinnati?

Yes. Swiatek recovered from losing the first set against Maria Sakkari to win 4-6, 6-1, 6-1 and reach the round of 16.

Is Coco Gauff still in Cincinnati?

Yes. Gauff came from behind to beat Liudmila Samsonova 2-6, 6-4, 6-1.

Why are Carlos Alcaraz and Jannik Sinner not on the failure list?

Neither played the tournament. Alcaraz withdrew because of a wrist injury, while Sinner withdrew with a right knee problem. Their absences are significant US Open stories but cannot fairly be categorized as Cincinnati match failures.

When does the Cincinnati Open end?

The 2026 Cincinnati Open runs through August 23, with both the men’s and women’s singles finals scheduled for the closing weekend.

The Sports Encounter’s tennis coverage follows ATP and WTA tournaments, player form, injuries, Grand Slam preparation, records and the performances shaping the biggest stories in the sport.