Over the years, Wimbledon has given us its fair share of memorable moments and great champions. And we have also witnessed our fair share of heart breaks. That is the nature of the sport, I guess. For every winner, there has to be someone who is the loser.

In this article, we look at the 10 most heart breaking losses in the history of the Championships.

10) 1981 Semi-final: Bjorn Borg – Jimmy Connors 0–6 4–6 6–3 6–0 6–4

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In 1981, Bjorn Borg was the 5 time defending champion. In 3 of those title runs, he had overcome Jimmy Connors, incuding twice in the finals. However, the 1974 champion, Connors was never one to throw in the towel. He had already stated that he wanted to win Wimbledon again. But to do that, he would need to overcome Borg in the semi-final.

This time, Connors raced off the blocks, taking the 1st set 6–0. Borg was being outplayed. Despite a better showing from the defending champion in the second set, Connors was still the man playing the better tennis, taking the second set 6–4.

Leading 2 sets to love, it looked as though Connors would finally be able to beat Borg at Wimbledon. But Borg was a fighter, and he came back to take the third 6–3. Borg then dominated the fourth set, getting a bagel of his own. The final set was a hard-fought affair, arguably the most even set of the match. Eventually Borg took it 6–4, and Connors once again ended up second best.

9) 2010 First-Round: John Isner – Nicolas Mahut 6–4 3–6 6–7 7–6 70–68

Wimbledon 2010 - Isner - Mahut; Longest Tennis Match Ever

Yes, there’s a first round encounter in our list of heart breaking Wimbledon losses. But this was no ordinary first round match. In fact, it was no ordinary tennis match.

At first, there was little interest in a first round matchup between the 23rd seeded John Isner and qualifier Nicolas Mahut. But as events started unfolding, interest grew as people realised that we were in the process of witnessing something extremely special.

A match like this is best described by a timeline:

Tuesday 22 June 2010

  • 6:13 pm – Match begins on Court 18
  • 6:45 pm – Isner wins the first set by 6–4
  • 7:14 pm – Mahut wins the second set by 6–3
  • 8:03 pm – Mahut wins the third set by 7–6, after winning the tiebreak 9–7
  • 9:07 pm – Isner wins the fourth set by 7–6, after winning the tiebreak 7–3. Play is suspended at two sets all. Total match time at this point was 2 hours, 54 minutes.

Wednesday 23 June 2010

  • 2:05 pm – Match resumes on Court 18 for the start of the fifth set
  • 5:45 pm – Match becomes the longest official match in history. The score at this point was 32–32 in the fifth set
  • 9:09 pm – Play is suspended for a second time, with the score tied at 59–59 in the fifth and deciding set. Total match time at this point was 9 hours, 58 minutes.

Thursday 24 June 2010

  • 3:40 pm – Match resumes on Court 18 at 59–59 in the fifth set.
  • 4:47 pm – Match ends in favour of John Isner, who won the final set 70–68. Total match time was 11 hours, 5 minutes.

A match played over 3 days; 11 hours and 5 minutes; 183 games; 980 points – and the rules of the game demand that their must still be a winner and a loser. Imagine being in Mahut’s shoes, who, after all that effort still didn’t make it past the first round.

By the latter stages of the second day, both players could barely move. But both kept fighting, and kept holding serve to take the match further and further. Ultimately Isner and Mahut fired down 113 and 103 aces respectively, and notched up 246 and 244 winners respectively. At the end, both players knew that they had been part of something special, but you still have to feel for someone who wins 91 games in a match and ends up losing.

8) 2012 Final: Roger Federer – Andy Murray 4–6 7–5 6–3 6–4

When Andy Murray reached his 1st Wimbledon final in 2012, there were huge expectations across the country. Could Wimbledon finally have its first British champion in 76 years? Murray had previously reached 3 major finals. He had lost all 3, 2 of those to Roger Federer. But Federer was now 30, and had not won a major since the 2010 Australian Open. The British media sensed an opportunity for Murray, highlighting the fact that he would be playing his first Wimbledon final against a 30 year old.

But Federer was no ordinary 30 year old. The first 2 sets were hard-fought affairs. Murray took the first set 6–4, Federer equalled the match taking the second 7–5. The final 2 sets weren’t nearly as close. Federer dominated the 3rd and 4th sets to wrap up victory in 4 sets.

Murray had been reduced to tears at the end. Britain’s wait for a home grown Wimbledon champion would continue. Murray’s wait for a first Grand Slam title would continue. He had now lost his first 4 Slam finals, 3 of those to Federer. An emotional Murray stated as he was left holding the runners-up plate, “He’s not bad for a 30 year old.”

Later that year, Murray would go on to win Olympic Gold and his first major title at the US Open. He would also win his first Wimbledon title the following year, finally ending Britain’s drought at the Championships.

7) 1970 Final: John Newcombe – Ken Rosewall 5–7 6–3 6–2 3–6 6–1

John Newcombe Ken Rosewall Wimbledon 1970

The great Ken Rosewall had just the Wimbledon title missing from his impressive trophy collection. He first won a major when he was just 18 years old. Before turning pro, he had won all the 3 Grand Slams barring Wimbledon. Now back in the Grand Slam circuit thanks to the start of the Open Era, a 35 year old Rosewall was looking to capture the 1 remaining major that would help him achieve the career Grand Slam. His opponent in the final was fellow Australian John Newcombe.

Rosewall took the first set, but Newcombe came back to take the second and third. Rosewall managed to extend take the match into a decider, but the final set proved a step too far for the aging Rosewall. Newcombe dominated the fifth set to take it 6–1.

Rosewall would later add to his Grand Slam collection, and to this day remains the oldest ever person to win a major title. However, Wimbledon would always remain unconquered territory for the man from Down Under.

6) 2001 Semi–final : Goran Ivanisevic – Tim Henman 7–5 6–7 0–6 7–6 6–3

Tim Henman vs Goran Ivanisevic Wimbledon 2001

Before Andy Murray, it was Tim Henman who carried the weight of British expectations on his shoulders. Losing semi-finalist in 1998 and 1999, it appeared as though Henman had finally received a golden opportunity to make it to the title round in 2001. This time, his opponent on the second Friday was unseeded Goran Ivanisevic. Ivanisevic was ranked 125th in the world and had been given a wildcard into the main draw. However, he was a 3 time runners up, and despite being arguably past his peak, his grass court pedigree was unquestionable.

Ivanisevic started brightly, and took the first set 7–5, getting the decisive break in the 12th game. The second set was a tense affair and neither player was able to grab a break. It went into a tiebreak, and Henman took a closely fought tiebreak 8–6 to level the match.

This spurred on Henman to greater heights. Under darkening skies, he played a sublime set of tennis to bagel Ivanisevic in the third. The set lasted barely 15 minutes, and Ivanisevic had won only 4 points throughout the entire set.

Ivanisevic’s fragile temperament was beginning to show through and he was on the point of collapse when, serving at 1–2 40–30, rain halted play. No more play was possible that day, and play had to resume on Saturday. That helped Ivanisevic regain his composure, while also cutting short Henman’s hot streak. Ivanisevic took the 4th set in another tiebreak, and we headed into a decider.

The final set was tied at 2–2, when rain once again halted play for the day, and the players had to come back on Sunday. The final was consequently shifted to Monday.

With the match so delicately poised at such an advanced stage, it was likely going to be a shootout, with the man who managed to strike first ending up the winner. That man was Ivanisevic, as he broke Henman to move ahead 5–3. He made no mistake in serving out the match, and Britain’s wait for a homegrown Wimbledon champion would continue.

While Tim Henman once again fell short of a maiden Grand Slam final, Ivanisevic was through to his 4th Wimbledon final, where he overcame Pat Rafter 9–7 in the fifth set to finally get his hands on the Wimbledon trophy. Henman ultimately never reached a major final, losing at the semi-final stage 6 times.

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