The 10 Greatest Wimbledon Matches of All Time – Ranked

June 26, 2025 Rasmus Kristensen

Wimbledon is the oldest and most prestigious tennis tournament in the world. Played on grass and steeped in tradition, it has hosted some of the sport’s most iconic moments and fiercest rivalries. Over the decades, tennis legends have battled on Centre Court in matches defined by brilliance, endurance, drama, and historical significance.

From epic five-set thrillers to record-breaking marathons, the following list celebrates the 10 greatest men’s matches in Wimbledon history — unforgettable clashes that left a lasting mark on the game and its fans.

10. Boris Becker vs Kevin Curren – 1985 Final

At just 17 years old, Boris Becker stormed onto the world stage by winning Wimbledon, becoming the youngest men’s champion in tournament history. Unseeded and relatively unknown, Becker’s fearless net play stunned Kevin Curren in four sets. This match marked the beginning of a new tennis era and a legendary Wimbledon career.

9. John Isner vs Nicolas Mahut – 2010 First Round'

Photo: Keith Sherwood / Shutterstock.com

In the longest match in tennis history, John Isner outlasted Nicolas Mahut in an 11-hour, 5-minute marathon spread across three days. The final set alone lasted over eight hours and ended 70–68. This epic changed the rules of tennis and redefined the limits of endurance and willpower.

8. Roger Federer vs Pete Sampras – 2001 Fourth Round

A young Roger Federer faced the reigning champion Pete Sampras in what became a symbolic changing of the guard. In a thrilling five-set battle, Federer stunned the tennis world by ending Sampras’ 31-match Wimbledon win streak. It was the only time the two legends ever played each other.

7. Pete Sampras vs Andre Agassi – 1999 Final

This all-American final showcased Pete Sampras at his clinical best. Dominating with his serve-and-volley mastery, Sampras overpowered French Open champion Andre Agassi in straight sets. It was one of Sampras’ finest Wimbledon performances and proof of his grass court supremacy.

6. Jimmy Connors vs Mikael Pernfors – 1987 Fourth Round

Down two sets and trailing 1–4 in the third, 34-year-old Jimmy Connors mounted an incredible comeback against the younger Mikael Pernfors. Battling injury and fatigue, Connors' gritty performance ignited the crowd and became one of the most iconic fights in Wimbledon history.

5. Novak Djokovic vs Roger Federer – 2019 Final

In the longest singles final in Wimbledon history, Djokovic and Federer battled for nearly five hours. It was the first Wimbledon final to be decided by a fifth-set tiebreak at 12–12. Djokovic saved two championship points and etched his name into history with an unforgettable win.

4. Andy Murray vs Novak Djokovic – 2013 Final

Andy Murray finally ended Britain’s 77-year wait for a men’s Wimbledon champion with a straight-sets victory over Novak Djokovic. The emotional win on Centre Court made history and confirmed Murray's place among the game’s greats. It was a moment of national pride and sporting triumph.

3. Roger Federer vs Andy Roddick – 2009 Final

Andy Roddick gave the performance of his life, but Federer edged him in an epic fifth set, 16–14. Roddick lost despite being broken only once in the entire match. With this victory, Federer secured his 15th Grand Slam title, surpassing Pete Sampras and cementing his legacy.

2. Björn Borg vs John McEnroe – 1980 Final

The clash of personalities — cool, stoic Borg versus fiery McEnroe — delivered one of the most legendary finals ever. McEnroe saved five match points in an unforgettable 18–16 fourth-set tiebreak before Borg sealed the win in the fifth. This match defined a generation and a rivalry.

1. Rafael Nadal vs Roger Federer – 2008 Final

Widely considered the greatest tennis match of all time, Nadal dethroned five-time champion Federer in a five-set epic. After nearly five hours and multiple rain delays, Nadal prevailed in the fading light, 9–7 in the final set. It was the ultimate battle between two legends at their peak.