Venus Williams walked off Arthur Ashe Stadium just after 2 a.m. Monday, her 26th U.S. Open singles run finished in the first round by Sofia Kenin. The final score was 6-2, 7-6 (6), a straight-sets defeat that stretched the 46-year-old's singles losing streak to 14 consecutive matches.

The match did not begin until 12:13 a.m. the latest start in U.S. Open history—six minutes past the previous record set by Aryna Sabalenka's match against Ekaterina Alexandrova in 2024. Novak Djokovic's first-round five-set loss to Mariano Navone, which ran four hours and 36 minutes, nearly pushed Williams and Kenin off Ashe entirely and onto Louis Armstrong Stadium. The men's match ended just in time to keep them on the main court.

Kenin, 27, needed just 32 minutes to close out the opening set. Williams clawed back from a 2-4 deficit to force a tiebreak in the second set, giving the crowd that stayed deep into the night a reason to cheer. She held set points in the tiebreak before sending a ball into the net to end the match at 2:01 a.m. the latest conclusion to a first-round match in tournament history and the third-latest finish for a women's match at any stage of the U.S. Open.

Williams' last singles win came in Washington in July 2025. She has now dropped six straight first-round matches at the U.S. Open, with her last win at the tournament coming in 2019. The 14-match losing streak covers her entire singles record since that Washington victory.

Williams won back-to-back U.S. Open titles starting in 2000. She also claimed five Wimbledon singles titles between 2000 and 2008, giving her seven Grand Slam singles crowns in total. She and her sister Serena combined for 14 Grand Slam doubles titles, including the U.S. Open doubles in 1999 and again in 2009. The two are entered in doubles again this year after receiving a wild-card entry.

Kenin, the 2020 Australian Open champion, earned a wild card for this tournament. Beating a seven-time Grand Slam singles winner in a match that started past midnight and stretched to 2 a.m. is a result that will follow her through the draw.

Djokovic's five-set loss to Navone was his first first-round defeat at a Grand Slam since 2006.