He Never Had an Easy Fight, Obi-Wan’s 10 Toughest Fights

As one of the principal characters in Star Wars, Obi-Wan Kenobi fought many duels. And there were times when he either barely won, or needed an ally to help him win or escape.

Not all of these fights came against Force-sensitives, either, showing us that you don’t need to wield the Force to qualify as a tough opponent. For example, two of Obi-Wan’s fights came against Mandalorians.

So which fights rank among Obi-Wan Kenobi’s toughest? Keep reading for the top ten.

1 – vs. Darth Vader in Obi-Wan Kenobi

Some may call this one recency bias, but the legendary fight between Darth Vader and Obi-Wan Kenobi in 9 BBY showed the Chosen One in his prime squaring off with a former master who had gone ages without using his Force-wielding powers.

Darth Vader knew he was the stronger opponent in this duel. And it didn’t take long until he buried Obi-Wan in a heap of rock. But the former Jedi Master broke free and launched a comeback, pelting Vader with boulder shards before he landed the winning blow.

This isn’t why his duel with Vader ranks number one on the list, though.

Kenobi’s reaction to seeing Vader’s face behind the busted mask set off an array of emotions. After a brief conversation with the Sith Lord, Kenobi realized that Anakin Skywalker was now consumed with the Darth Vader identity.

2 – vs. Count Dooku in Revenge of the Sith

You will see this one clock in at number one on many lists, since Obi-Wan Kenobi would not have won this fight without Anakin Skywalker’s help. In fact, Dooku overpowered Kenobi, forcing Anakin to duel the Sith Lord one-on-one.

While Kenobi wouldn’t see it occur, what makes this fight one of the toughest ever was the fact that it gave Chancellor Palpatine an opportunity to drive Anakin closer to the dark side.

The Jedi Knight had Dooku beaten, and Palpatine urged him to kill the Sith Lord. Anakin hesitated before he decapitated Dooku.

3 – vs. Count Dooku in Attack of the Clones

Three years before Obi-Wan and Anakin’s fight against Count Dooku over Coruscant, the duo crossed paths with him in 22 BBY during the events of Attack of the Clones.

This one occurred during the Battle of Geonosis, and it wasn’t long before Dooku got the best of Obi-Wan and Anakin, with the latter losing an arm in the process.

While Kenobi and Skywalker lost this battle, they escaped thanks to an intervening Yoda. The Jedi Master dueled his former apprentice, proving he was still the stronger Force-wielder.

4 – vs. Darth Vader in Revenge of the Sith

One of the most legendary lightsaber duels in the Star Wars franchise, Obi-Wan was forced to confront Anakin Skywalker, who was now going by the moniker Darth Vader.

They met on Mustafar, shortly after Vader Force-choked his wife, Padme. Following a brief verbal dispute, Vader struck first, and the former friends ended up dueling over the lava river.

No one managed to gain the upper hand until Obi-Wan jumped onto the shore littered with volcanic rock, proclaiming, “I have the high ground.”

This further angered Vader who, despite Obi-Wan’s warnings, tried to continue the fight. However, the Jedi Master sliced off his former apprentice’s arm and legs, leaving only the prosthetic arm intact.

5 – vs. General Grievous in Revenge of the Sith

The Jedi Council sent Obi-Wan Kenobi to Utapau to confront General Grievous. And while Grievous was not Force-sensitive, he was proficient in lightsaber combat thanks to Count Dooku.

Though Grievous wielded four lightsabers, Kenobi proved to be more skilled, forcing the Separatist war lord to find another way to try and defeat the Jedi Master.

Grievous gained the upper hand late in the battle. But Obi-Wan, in a last-ditch attempt to defeat the Separatist leader, grabbed a blaster and fired several shots into Grievous, killing him.

6 – vs. Darth Maul in The Phantom Menace

In The Phantom Menace, Obi-Wan Kenobi and his master, Qui-Gon Jinn, first encountered Darth Maul on Tatooine. Qui-Gon fought off the Sith Lord, but they met again during the Battle of Naboo.

Despite the duo putting up a respectable fight, Maul gained the upper hand and killed Qui-Gon. He turned his attention to Obi-Wan, who went on the offensive, matching Maul strike for strike.

Kenobi displayed such proficient lightsaber skills, he forced Maul to retreat. But the Sith Lord battled back, and the two once again traded strikes.

Maul landed a kick to Kenobi, sending the Padawan toward a shaft. Kenobi would have fallen to a presumed death, but he grabbed onto a light protruding from the cylindrical wall.

Maul, however, found Obi-Wan’s lightsaber and kicked it down the shaft, before approaching to land a potential death blow. Using the Force, Kenobi catapulted himself toward Maul while summoning the lightsaber of his fallen master.

This enabled Obi-Wan to slice Maul’s midsection, sending the Sith Lord falling down the shaft. Maul was thought to be dead, but he re-emerged during The Clone Wars.

7 – vs. Maul and Savage Opress in The Clone Wars

Obi-Wan Kenobi twice faced Savage Opress and Maul in The Clone Wars during Seasons 4 and 5.

For years, Obi-Wan thought Maul was dead, but he crossed paths with the former Sith Lord and his brother in Season 4 of The Clone Wars. And if it wasn’t for Asajj Ventress, Obi-Wan may not have beaten the Force-sensitive siblings.

In the Season 5 premiere, Obi-Wan again faced off with the brothers. This time, he had Adi Gallia on his side, but Savage Opress killed her, forcing Kenobi to fight the powerful Force-sensitive brothers.

Obi-Wan escaped once again, showing off some of his best-ever lightsaber skills in the process.

8 – vs. Jango Fett in Attack of the Clones

In Attack of the Clones, the Jedi Council tasked Obi-Wan Kenobi with locating Senator Padme Amidala’s would-be assassin. During his investigation, Kenobi ended up on the planet Kamino, where he discovered its inhabitants manufacturing a clone army.

Famous bounty hunter Jango Fett served as the template for these clones, and Kenobi realized that he was the one behind the plot to assassinate Padme. This led to a confrontation and subsequent duel between the bounty hunter and the Jedi Knight.

Despite not being Force-sensitive, Jango held his own against Obi-Wan, showing us how well Mandalorians match up against the Jedi. However, regardless of what Jango tried throwing at Obi-Wan, he couldn’t overpower him.

One caveat with this battle is that Obi-Wan needed to bring in Jango alive. If that wasn’t the case, then perhaps this fight could have gone in a different way.

9 – vs. Pre Vizsla in The Clone Wars

We saw the Darksaber debut when Obi-Wan fought Pre Vizsla, who put up an incredible fight against the Jedi Master. Not only did Pre Vizsla show off remarkable skills with the Darksaber, he also caught Kenobi off-guard with an entertaining display of martial arts.

But as Pre Vizsla moved in to strike a death blow, Kenobi fought back, showing off his own skill in hand-to-hand combat, gaining the upper hand and winning the fight.

This caused Pre Vizsla to order his Mandalorian warriors to finish off Kenobi, but he and Satine escaped the blasts. While the warriors asked if they should continue pursuing Kenobi, Pre Vizsla refused to continue the chase, citing lack of time.

10 – vs. Acklay in Attack of the Clones

Few would add Obi-Wan Kenobi’s fight with Acklay to the list, but during their meeting in Attack of the Clones, Obi-Wan found himself in quite a vulnerable spot.

Chained to a stake, Obi-Wan was forced to use his enhanced speed and agility to defend himself against Acklay’s attacks. He eventually outsmarted the beast long enough to break free, find a lightsaber, and win the fight.

While this wasn’t a traditional lightsaber duel, it’s significant in the fact that it showed us Obi-Wan doesn’t always need to wield a lightsaber to win. Instead, he can rely on the Force and his own smarts to defeat any opponent.

Sion Fawkes

Sion Fawkes has been covering Star Wars since January 2022, expanding his expertise in Star Wars Canon, Legends, and MCU. When not writing, you can find Sion in the gym or running trails. He also likes watching sports and listening to audiobooks.