Obi-Wan Kenobi and Darth Maul share a long and bitter history in Star Wars canon, engaging in lightsaber duels on four different occasions, with wins on both sides. The two first crossed paths in 1999’s Star Wars: The Phantom Menace, and for years the Sith apprentice was believed dead. Maul was eventually resurrected towards the end of the fourth season of the television show Star Wars: The Clone Wars, paving the way for some exciting rematches with his old foe.

Darth Maul - a Dathomirian Zabrak and the former apprentice of Darth Sidious - was once thought to be a one-and-done villain, killed off before reaching his full potential. Thankfully, Maul returned to screens 13 years later in animated form. Hell-bent on enacting revenge against Obi-Wan, he spent years of his life stalking the Jedi Master, creating one of the longest rivalries in Star Wars canon.

Related: The Clone Wars Fixed Phantom Menace’s Darth Maul Mistake

This may come as a surprise to casual filmgoers, as Maul didn’t return in live-action until his surprise cameo at the end of 2018’s Solo: A Star Wars Story. The enemies dueled across four planets in the Star Wars timeline, but only one would ultimately survive the conflict. Obi-Wan and Maul’s relationship significantly expanded since their first encounter. Their fights provided some of the most thrilling lightsaber action in canon, but there were also a few tender moments that deepened their understanding of one another.

Duel of the Fates: Obi-Wan & Qui-Gon vs. Maul

Obi-Wan and Qui-Gon fighting Darth Maul in the Duel of the Fates in The Phantom Menace

Acting as the memorable climax of the otherwise disappointing The Phantom Menace, the first duel between these characters remains arguably the greatest of the entire franchise. While Queen Padmé Amidala leads a strike team to defeat the Trade Federation during the Battle of Naboo, Obi-Wan and Qui-Gon confidently decide to take care of the mysterious Sith. Backed by John Williams’ epic score, this duel plays like an expertly choreographed ballet, which is in stark contrast to the slower, more methodical lightsaber fights in the original trilogy.

Obi-Wan may already be a skilled swordsman, but he is still an apprentice at this point in the Star Wars canon, and it shows in his fighting style. He adopts the same Ataru stance as Qui-Gon, incorporating many flips into the duel. He exhibits some similarities to Maul through the habit of twirling his lightsaber in his hand, getting a feel for the weapon’s weight. However, Maul is considerably more agile and exploits the pair’s weaknesses. Obi-Wan is inexperienced in the Ataru form and easily knocked aside, while Qui-Gon shows his age. Nevertheless, master and apprentice illustrate their considerable teamwork, such as Obi-Wan agitating Maul by feigning an attack, only for Qui-Gon to lunge at the Sith. Maul is an adept warrior but also knows his limits. He separates the pair, leading them through the power generator until they are all stuck between energy fields.

This scene doesn't need dialogue to effectively reveal the differences in the trio’s characterization. Obi-Wan is young and impatient, desperate to reach his master. Similarly, Maul paces in anger. Only Qui-Gon waits peacefully. It’s not enough to save Qui-Gon, and when Maul strikes him down, Obi-Wan is overcome with rage. This gives Maul the upper hand, using the force to push Obi-Wan into a large pit. It’s a calm, clear mind that wins the day, with Maul looking on in utter confusion as Obi-Wan concentrates on channeling the force to thrust himself out of the pit, leaping over Maul to slice him in half. It’s a move that the more frenzied Maul never anticipated, while Obi-Wan learned from his mistakes for future Star Wars battles.

Related: How Maul Gets From Clone Wars to Solo & Rebels 

Obi-Wan & Asajj Ventress vs. Maul & Savage Opress

Darth Maul with his new mechanical legs in Star Wars The Clone Wars

It took him over 10 years, but Maul finally returned with a vengeance in “Revenge”, the season 4 finale of Star Wars: The Clone Wars. Having regained his memory and a new pair of robotic legs after a visit to Mother Talzin on Dathomir, Maul works alongside his brother, Savage Opress, to lure his old enemy into a trap. Threatening Obi-Wan with the slaughtering of innocent civilians on the planet of Raydonia, the stage is set for a rematch. However, Maul fails to take advantage of the moment Obi-Wan is knocked unconscious and instead takes him aboard his ship to slowly torture him to death. His delay allows time for assassin Asajj Ventress to arrive, looking to claim the bounty on Opress’ head. What could have been an instant kill suddenly becomes a more even duel. Obi-Wan has become an even greater fighter over the years, switching from Ataru to Soresu.

Obi-Wan learned from the weaknesses of his master’s fighting form, but Maul remains a formidable opponent, quickly adapting to his new legs and using them as a means of fiercely kicking Obi-Wan across the room. Years of resentment kept Maul alive, and Obi-Wan struggles to fend off such hate, even with Ventress present to distract Opress. Maul recalls how he almost defeated Obi-Wan the first time and taunts him over the murder of Qui-Gon. An angered Obi-Wan gets sloppy, with careless swings slashing only the ship's surroundings. As Maul mockingly comments, “Your rage unbalances you. That is not the Jedi way.” Later Star Wars stories show Obi-Wan would eventually overcome the error of sacrificing accuracy for bursts of fury, but it’s clear Maul is one of the few people who can get under his skin. Obi-Wan suggests to Asajj that they retreat, making a run for the cockpit and narrowly escaping Maul’s ship. While neither gets what they want from the duel, Obi-Wan’s unbalanced emotions can be seen as a figurative victory for Maul.

Obi-Wan & Adi Gallia vs. Maul & Savage Opress

Obi-Wan faces off with and outsmarts Maul and Savage Opress In Star Wars The Clone Wars

Maul and Obi-Wan face off again in the very next installment - Star Wars: The Clone Wars season 5, episode 1, "Revival". Hunted by the Jedi Order, Maul and Opress look to recruit an army by forcing Hondo Ohnaka’s pirates to pledge their allegiance. Hondo refuses to serve Maul and works alongside Obi-Wan and fellow Jedi, Adi Gallia, leading to a battle with the dissenting pirates on Florrum. As with their last encounter, Obi-Wan duels with Maul, while Gallia battles Opress separately. She is unable to defeat Opress, who rams her with his head, horns piercing her torso. Obi-Wan’s attempt to kill Opress in retribution is swiftly blocked by Maul, but he doesn’t give in to anger on this occasion. Obi-Wan demonstrates a more tactful approach, especially when an even fight is reduced to two Dathomirians against one Jedi. Still, Obi-Wan is almost overpowered.

Trapped on the ground with his back against a wall, he struggles to fend off his opponents, until he spots a weakness in Opress’ footing. Obi-Wan kicks his knee and seizes the opportunity to sever Opress’ arm, prompting a panicked Maul to force-push Obi-Wan across a corridor, with the ceiling collapsing to form a wall between them. The duel demonstrates Maul’s loyalty to his brother, proving that he does care for Opress as more than merely his apprentice. Throwing Obi-Wan out of the way may have also been a tactical decision, but it’s a moment where Maul prioritizes family over revenge, even if it is brief. The duel is a stalemate, with injuries on both sides. However, Maul’s subsequent retreat can be viewed as a slight victory for Obi-Wan.

Related: Star Wars Rebels: Why Maul Was Looking For Obi-Wan (Not To Kill Him)

Obi-Wan vs. Maul

Obi-Wan vs. Darth Maul in Star Wars: Rebels, Twin Suns

While the pair did cross paths twice more, during Maul’s takeover of Mandalore in season 5, and during the Son of Dathomir tie-in comic, they never actually dueled again until Star Wars: Rebels season 3, episode 20, “Twin Suns”. Set during the Imperial Era, Maul’s hatred for Obi-Wan finally dissipates in the Tatooine desert, roughly 30 years after their first encounter. By this point, both characters have suffered immensely. The Jedi are all but extinct and Maul’s numerous attempts to gain power have failed. Manipulating Ezra Bridger into leading him to Obi-Wan, the final duel suitably feels like a last-ditch attempt to relive the past.

Obi-Wan initially appears reluctant to fight, advising Maul to relinquish his hate. Only after Maul realizes the Jedi is protecting someone does he play along. Switching between Alec Guinness’ stance from Star Wars: A New Hope, Soresu, and finally, Ataru, Obi-Wan shows his evolution in combat style and maturity, while leading Darth Maul into a false sense of security. Attempting to kill his rival in the same manner as he did Qui-Gon, Maul shows his inability to move on from the past. The duel is over within seconds. Using just a few swipes, Obi-Wan predicts Maul’s moves and slashes him down the chest. Despite everything that occurred between the pair, Obi-Wan still holds Maul as he dies in his arms – a touching goodbye to his old life before the Empire. Obi-Wan has vanquished his enemy, but it’s a hollow victory.

Each duel defines their evolving characters over the course of the Star Wars canon. Obi-Wan and Maul were almost perfectly matched, but the latter’s overconfidence continually proved to be his undoing. Obi-Wan changed combat styles to better defend himself, becoming far more precise and less acrobatic over the years. Maul remained consistent to the end, blinded by rage. While not the only opponent to defeat Darth Maul in battle, Obi-Wan seemed to be considered his equal, and Maul was lost without him. Obi-Wan’s hope for Luke Skywalker kept him focused during his self-imposed exile, but his reaction to Maul’s death suggests there was no true victor in the end.

Next: Darth Maul's Star Wars Future Explained: What Movies & Shows He Could Appear In