Ken Rosewall’s 1974 US Open final loss to Jimmy Connors was completely lop-sided // Picture Courtesy — Tennis World
Roger Federer’s loss to Novak Djokovic in the 2011 semifinals was a bitter blow.
The US Open has seen its share of stunning defeats and unexpected losses. These moments are etched in history not just for their shock value, but also for the emotional and competitive impact they had on players and fans alike. Here, we explore some of the most disappointing losses in US Open history based on major upsets, missed opportunities, and poor performances in critical matches.
Pete Sampras’ loss to Lleyton Hewitt in the 2001 US Open finals marked a significant blow to Sampras’ comeback hopes. After a period of declining form, Sampras managed to reach the finals but was outplayed in straight sets by Hewitt, who won 7–6, 6–1, 6–1. Despite a strong start, Sampras struggled with his game, and his serve, usually his strength, faltered. The defeat was a disappointment for Sampras, who had hoped to capture his 14th Grand Slam title.
Ken Rosewall’s 1974 US Open final loss to Jimmy Connors was notable for its one-sided nature. At 39, Rosewall aimed to become the oldest Grand Slam champion but was crushed 6–1, 6–0, 6–1 by the 22-year-old Connors. The defeat was especially painful for Rosewall and his supporters, as it was the most lopsided men’s final in the Open Era. This match marked the end of Rosewall’s chance at another major title.
Andy Roddick’s first-round exit to Gilles Muller in the 2005 US Open was a major upset. Roddick, a former US Open champion and a high seed, lost in three tiebreak sets to Muller, ranked №68 and making his debut in the main draw. Roddick’s early exit was compounded by the fact that it occurred on his 23rd birthday, leaving him in shock and disappointment.
Stefan Edberg’s unexpected first-round loss to Alexander Volkov in 1990 was one of the biggest upsets in US Open history. Edberg, the defending champion and top seed, lost in straight sets, 6–3, 7–6, 6–2, to a player ranked №52. Edberg’s loss was a significant shock, given his strong performance in the lead-up to the tournament and his previous success on hard courts.
Ana Ivanovic’s second-round loss to Julie Coin in the 2008 US Open was a major surprise. Ivanovic, ranked №1 and the French Open champion that year, was defeated by the then №188-ranked Coin in a three-set match. Coin’s victory was notable not only for its unexpected nature but also for the fact that Ivanovic was far from her best, contributing to a disappointing early exit.
Guillermo Vilas’s loss to Manuel Orantes in the 1975 semifinals was particularly disheartening. Vilas, a dominant clay-court player, had several match points but failed to close out the match, ultimately losing 4–6, 1–6, 6–2, 7–5, 6–4. This defeat was frustrating for Vilas, who was expected to win and went on to see Orantes win the title the following day.
Roger Federer’s loss to Novak Djokovic in the 2011 semifinals was a bitter blow, following a similar heartache from the previous year. Federer held double match points in both the 2010 and 2011 semifinals but failed to convert either time. In 2011, despite being up two sets to one and having match points while serving, Federer lost in five sets, 6–7 (7–9), 4–6, 6–3, 6–2, 7–5.
Bjorn Borg’s loss to John McEnroe in the 1981 finals symbolized the end of an era. Borg, who had dominated the sport in the late 1970s, appeared disinterested and failed to maintain his level of play after winning the first set. McEnroe dominated the rest of the match, winning 4–6, 6–2, 6–3, 6–4. Borg’s abrupt departure from the sport post-match was a significant letdown for fans and marked a notable shift in tennis history.
Andrea Jaeger’s shocking loss to Andrea Leand in the 1981 US Open second round was marked by a dramatic collapse. Jaeger, a high seed, was leading 6–1, 5–2 before losing the match 1–6, 7–5, 6–3. The defeat was especially disappointing as Jaeger had a substantial lead and failed to convert multiple match points.
Martina Navratilova’s first-round loss to Janet Newberry in 1976 was a crushing blow. Navratilova, a rising star and №3 seed, lost 1–6, 6–3, 6–3 after taking the first set easily. Her visible distress and emotional breakdown post-match underscored the depth of her disappointment, marking one of the most emotionally charged losses in US Open history.
