The 10 Most Heart Breaking Losses In Wimbledon History (5-3)

5) 2008 Final: Rafael Nadal – Roger Federer 6–4 6–4 6–7 6–7 9–7

Wimbledon 2008 Federer vs Nadal

The 2008 final was set up to be an epic. Federer had been suffering from mononucleosis for the first half of the season and was experiencing his worst season in years. He had been demolished by Rafael Nadal in the French Open final 4 weeks back. Nadal on the other hand, was in rampant form having bulldozed his way through another clay court swing, culminating in him winning the French without dropping a set.

But Wimbledon was Federer’s backyard, and having been unbeaten on grass for nearly 6 years, Federer was still considered the favourite by most people. However, no one expected it to be easy. Fedal matches rarely were.

Rain delayed the start of the match by 35 minutes, but once things got underway, we were treated to a spectacle. In the first set, Federer put pressure on the Nadal serve, but Nadal held on. Ultimately it was Nadal who got the decisive break to take the set 6–4. Nadal would again end up taking the second set 6–4. Federer had his chances too, but so far Nadal had done a better job of grabbing his.

Rain stopped play with Federer leading the 3rd set 5–4. The players returned on court after an 80 minute delay. Federer took the 3rd set in a tiebreaker. The 4th set was another tight affair, which needed another tiebreak to decide the outcome. And this time, the breaker was an epic. Nadal brought up Championship point on his serve with a brilliant passing shot. Federer saved it with an even better passing shot of his own to level at 6–6. Nadal brought up a second Championship point, but Federer again saved it, with a big first serve this time. Federer eventually went on to take the breaker 10–8 and level the match at 2 sets all.

The momentum was now firmly with Federer. But with the score tied at 2–2 in the final set, another rain delay would prove decisive. When the players came back on court, darkness had started setting in. Nadal emerged the stronger of the two, but Federer fought valiantly to keep up with the Spaniard. Nadal eventually got the decisive break to go up 8–7. In near darkness, Nadal served out the match to end the epic encounter and Federer’s run of dominance at the Championships.

In the end, one stat stood out more than any other – Federer had managed to convert only 1 of 13 break point opportunities. Federer had had his chances, but he just didn’t take them as well as his opponent. The following year, Federer would bounce back to reclaim his crown in yet another epic final.

4) 1998 Final: Pete Sampras – Goran Ivanisevic 6–7 7–6 6–4 3–6 6–2

Ivanisevic vs Sampras Wimbledon 1998 Final

The mercurial Goran Ivanisevic reached his 3rd Wimbledon final in 1998, having come through a marathon semi-final battle against Richard Krajicek. He had lost his 2 previous finals to Andre Agassi and Pete Sampras respectively.

This time his opponent was once again Sampras, who was gunning for a record-equalling 5th Wimbledon title. Sampras knew he had a battle on his hands against the big-serving Croat.

The first set was a tight affair, but Ivanisevic drew first blood taking it in the tiebreak. The second set went to another tiebreaker. Both players had their chances and had set points. However, it was Sampras who prevailed 11–9, and levelled the match.

Sampras took the 3rd set, and Ivanisevic fought back to take the 4th. Thus, it went down to a final set, and Ivanisevic would’ve fancied his chances. However, Sampras raised his game and broke Ivanisevic twice in the final set to take it 6–2. Perhaps, Goran’s tough semi-final had taken its toll in the final set. Sampras went on to lift his 5th Wimbledon trophy, while Ivanisevic was still left waiting for his maiden title.

3 years later, Ivanisevic would finally win Wimbledon following a fairy-tale run having entered the draw as a wildcard. That would undoubtedly go down as one of the greatest feel-good moments in the history of the Championships.

3) 1989 Semi–final: Boris Becker – Ivan Lendl 7–5 6–7 2–6 6–4 6–3

There’re a lot of theories regarding what Ivan Lendl could’ve done differently in order to win Wimbledon. What must not be forgotten however is how close he actually came to winning it, on multiple occasions. He had reached the 1986 and 1987 finals losing to Boris Becker and Pat Cash respectively. In 1989, he reached the semi-finals for the 4th consecutive year, and the 6th time in 7 years. Having won the Australian Open earlier that year, Wimbledon was the only major missing from his Grand Slam cabinet.

His semi-final opponent was the grass-court specialist, Boris Becker, who had defeated him in the 1986 final and the semis of the previous year. Becker was in fine form, reaching the semis without dropping a set. But Lendl was constantly working hard to improve his grass court game, and this time he seemed better prepared than ever.

The match was a 4 hour classic, with both players pushing each other to the limit. Becker took the first set 7–5. Lendl took the 2nd in a tiebreaker, and then raised his game to take the 3rd 6–2.

In the 4th set, Lendl went up an early break. But a rain delay caused the momentum to swing Becker’s way. Becker fought back to win the 4th 6–4. The final set went on serve for the first 7 games. But Becker managed to break Lendl in the 8th to go up 5–3. He promptly served out the match without any drama.

Lendl cut a dejected figure at the end. There was no questioning how much he wanted it, and how much he had worked for it, despite not being a natural on grass. He left the centre court shaking his head.

The following year, Lendl skipped the French Open in order to give himself an even better shot at Wimbledon. He once again made it through to the semi-final stage, but lost to Stefan Edberg. When he retired, he had won all the other 3 Slams multiple times. Wimbledon however, remained unconquered!

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