Novak Djokovic arrives at the 2026 US Open with a second piece of history within striking distance. Beyond his pursuit of a 25th Grand Slam title, the Serbian is only four match victories away from becoming the outright leader for singles wins at Flushing Meadows.
The equation is unusually simple.
Jimmy Connors remains at the top of the US Open singles wins list with 98 victories, accumulated between 1971 and 1992. Djokovic begins this year’s tournament on 95, while Roger Federer sits third on 89.
That leaves Djokovic three victories short of drawing level with Connors and four away from moving ahead.
If he wins his opening three matches in New York, Djokovic will reach 98 US Open victories and match Connors. One more victory, in the round of 16, would take him to 99 and give him the record outright.
Novak Djokovic’s road to 99 US Open wins
Djokovic will begin his 2026 campaign against Mariano Navone.
A victory there would set up a second-round meeting with the winner of Matteo Berrettini against Stan Wawrinka. The potential third-round opponents identified in the draw are Tomas Martin Etcheverry or Martin Landaluce.
Getting through those first three rounds would be enough to bring Djokovic alongside Connors on 98.
The record-breaking match could then arrive in the fourth round. American Brandon Nakashima is among the players Djokovic could potentially encounter at that stage.
It gives the early rounds of Djokovic’s US Open an additional layer of significance. His progress will not only determine whether another Grand Slam title remains possible, but could also steadily erase one of the few major tournament records he has yet to claim.
Connors’ US Open benchmark has stood for decades
Connors built his total of 98 US Open singles victories across a career at the tournament that stretched from 1971 to 1992.
His record was accompanied by five US Open titles, won during the period between 1974 and 1983.
Djokovic enters the 2026 tournament only three victories behind that total despite already holding a six-win advantage over Federer in the US Open career standings.
The immediate milestone comes before the latter stages of the tournament. Djokovic does not need to reach another semifinal or final to take the record. A place in the quarterfinals would mean he has won four matches, moving his US Open total from 95 to 99.
A 25th Grand Slam remains the bigger prize
The US Open wins record is not the only number surrounding Djokovic in New York.
Winning the tournament would give him his 25th Grand Slam singles title. His most recent US Open championship came in 2023, when he defeated former world No. 1 Daniil Medvedev in the final to claim the 24th Major of his career.
His 2025 campaign ended one stage earlier. Djokovic reached the semifinals in New York before losing to Carlos Alcaraz.
That recent history makes the 2026 tournament notable on two fronts. A deep run could put Djokovic back in contention for another Grand Slam trophy, while even a quarterfinal appearance would be enough to place his name alone at the top of the US Open singles wins list.
Is this really Djokovic’s last chance?
There is no information here confirming that the 2026 US Open will be Djokovic’s final opportunity to break Connors’ record.
What can be established is considerably more concrete: Djokovic begins the tournament on 95 victories, Connors holds the benchmark at 98, and four wins would settle the record in Djokovic’s favour.
For now, that makes the fourth round potentially more consequential than usual. Should Djokovic survive his first three matches, his next appearance would offer the chance to turn a long-standing US Open record from 98 into 99.
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