Obi-Wan Kenobi and General Grievous fought a number of times in Revenge of the Sith, his role as Obi-Wan's foil would be significantly expanded in other Star Wars media. Each encounter would challenge Obi-Wan in different ways, resulting in noticeable character developments, as their duels persisted throughout the war. This rivalry between Obi-Wan and Grievous recontextualizes their final encounter in Revenge of the Sith and gives new meaning to the final outcome.
The duels between Jedi Master Obi-Wan Kenobi and General Grievous are fascinating because of how each character changed over time. Both opponents learned more about the other with every encounter, and the outcome of one duel determined how they would approach the next. Fighting General Grievous also brought out a different side of Obi-Wan as the war progressed, which very well could have consumed him by the end. However, the same can be said for Grievous, and despite the various wins and losses, their rivalry had to conclude eventually.
Star Wars: Hyperspace Stories #1
Obi-Wan Kenobi's first duel with General Grievous in Star Wars canon occurred in the first issue of the Hyperspace Stories comic series. On a mission to rescue Pé Amidala, Obi-Wan and Anakin Skywalker split up so that Obi-Wan could rescue a Wookiee senator and his daughter from General Grievous. The two engaged in a brief lightsaber duel before Senator Yarua sacrificed himself by tackling Grievous out of an airlock. Though Obi-Wan believed Grievous may have been killed, Yoda warned him that the droid general should not be underestimated.
This was one of the shortest duels between Obi-Wan and Grievous in canon, and neither had a chance to really test the other. However, this would be Obi-Wan's first time witnessing Grievous' ruthless and cowardly nature, willing to threaten a child rather than surrender. Grievous also learned that Obi-Wan holds great comion for the innocent, which could be used against him in the future. Though their first duel ended in a stalemate, Obi-Wan and Grievous would have many more before the end of the Clone Wars.
Star Wars Adventures: The Clone Wars - Battle Tales #5
The next duel between Obi-Wan Kenobi and General Grievous took place in the final issue of The Clone Wars: Battle Tales comic series. Obi-Wan and his troops were captured by Grievous and forced to rebuild a bridge for Separatist forces to cross. The planet's natives agreed to help by retrieving Obi-Wan's lightsabers and attacking Grievous's forces. An enraged Grievous attacked Kenobi, who lured him onto the bridge and used the Force to bring an avalanche of snow that swept away Grievous and his battle droids.
Obi-Wan demonstrates his trademark use of humor to mock and anger Grievous, a tactic he would use in future confrontations with the general. He also calls Grievous Dooku's pet, which infuriates the general and causes him to lash out. Other Jedi would mock and joke about General Grievous on this point as well, but with this being an early confrontation in the war, Obi-Wan could use it to get under Grievous' skin. With Separatist forces closing in, Obi-Wan was willing to leave Grievous behind, which would not always be the case for their later duels.
Star Wars: The Clone Wars season 1, episode 4 "Destroy Malevolence"
Star Wars: The Clone Wars presented the first on-screen duel between Obi-Wan Kenobi and General Grievous in the Star Wars canon timeline. Once again tasked with rescuing Pé Amidala, Obi-Wan, and Anakin Skywalker snuck aboard Grievous' flagship, the Malevolence, which was in retreat from Republic forces. Obi-Wan went to disable the ship's hyperdrive, finding himself surrounded by Grievous's battle droids, which he was able to defeat before escaping. Grievous chased after Obi-Wan, and the two fought on top of a hovertrain before Obi-Wan was finally able to get away.
Although Obi-Wan managed to escape, this was the first time Grievous truly gained the upper hand in combat. Grievous was ready to strike his opponent down, which Obi-Wan narrowly avoided by rolling off the side of the hovertrain. The encounter taught Grievous that Obi-Wan could easily handle being surrounded by regular battle droids, as well as reinforcing Anakin and Obi-Wan's go-to strategy for rescuing prisoners. This would also be the last duel laced with humor and banter before Obi-Wan and Grievous' rivalry began taking a darker turn.
Star Wars: The Clone Wars season 2, episode 9 "Grievous Intrigue"
Obi-Wan and Grievous' next duel in Star Wars canon was in The Clone Wars season 2. The Jedi mounted a rescue mission for Master Eeth Koth, with Obi-Wan distracting Grievous while the others snuck onto his ship. However, Grievous' was now all too familiar with Obi-Wan and Anakin's rescue strategy, and had a squad of commando droids lying in wait for them. The Jedi did save Master Koth, but Grievous was able to escape to the planet below.
This duel marked several changes for Obi-Wan and Grievous. Obi-Wan became much more serious from that point on, being noticeably agitated and disappointed at Grievous' escape. Unlike their encounter in Battle Tales #5, Grievous did not give in to reckless anger when Obi-Wan insulted him about being Dooku's puppet, or for anything else. Both opponents also knew each other well enough to guess the other's tactics: Obi-Wan knew Grievous would want to face him personally, and Grievous knew what Obi-Wan's most likely strategy would be. This game of wits would make it increasingly difficult for Obi-Wan or Grievous to triumph over the other.
Star Wars: The Clone Wars season 2, episode 10 "The Deserter"
Obi-Wan and Grievous would duel again in the following episode of The Clone Wars season 2. The Republic forces pursued Grievous down to the planet Saleucami, attempting to cut him off before he could escape in a shuttle. Obi-Wan caught up to Grievous and the two engaged in a fierce lightsaber duel, but Grievous was able to escape once again. Coming so close to capturing Grievous, only to lose him a second time, left Obi-Wan understandably angry, noting that they were right back where they started.
Grievous' escape solidified Obi-Wan's shift in attitude for most of their future encounters. Obi-Wan had developed a new level of seriousness with regards to Grievous, with a greater determination to stop him once and for all. While Grievous would eventually use that to his advantage, he didn't bother with words in this duel, focusing entirely on escape at all costs. Grievous would increasingly threaten to bring out Obi-Wan's dark side and constantly remain out of reach.
Star Wars: The Clone Wars season 3, episode 2 "ARC Troopers"
Obi-Wan and Grievous would meet again in The Clone Wars season 3, during the Separatist invasion of Kamino. Having changed after their last encounter, Obi-Wan wasted little time on words, moving quickly to meet Grievous in combat. Grievous took advantage of his extra limbs to gain the upper hand, but Obi-Wan was able to counter with a series of Force attacks. After retreating to a landing platform, the two locked blades again, before Grievous was able to escape after Kenobi fell off the side.
While Obi-Wan was determined in their duel on Saleucami, he was full-on angry fighting Grievous on Kamino. This is understandable, as Grievous was attempting to kill the entire clone army, on top of the mark left by their last meeting. Grievous made a greater attempt to get in Obi-Wan's head, telling him that Kamino had fallen and that all the Clones would be next. Obi-Wan also demonstrated Grievous' inability to counter a concentrated Force attack, which it seems the general never fully learned from.
Star Wars: The Clone Wars season 5, episode 8 "Bound for Rescue"
General Grievous would not face Obi-Wan Kenobi again until The Clone Wars season 5. Before Obi-Wan could launch a rescue mission to save Ahsoka Tano, his fleet was ambushed by Grievous, who boarded Obi-Wan's ship and overwhelmed his forces. Grievous came face-to-face with his old enemy, laughing as he crushed the life out of a helpless clone soldier. Obi-Wan's only reply was an angry "You'll regret that," before the two locked blades once again. Grievous defeated Star Wars' Obi-Wan Kenobi, forcing him and his men to abandon the ship, but not before initiating the self-destruct, which Grievous barely escaped.
Grievous made Obi-Wan mad at Kamino, but the droid general finally pushed him into fighting with a desire for revenge. Their very first encounter had taught Grievous to use the defenseless against Obi-Wan, made even worse by his laughing about it. This was also the first time since their duel on the Malevolence that Grievous was the clear-cut winner in combat, as Obi-Wan was forced to retreat. Initiating the ship's self-destruct showed that Obi-Wan would rather destroy his own ship than let Grievous have it, especially if it meant taking Grievous down with it.
Star Wars: The Clone Wars - "The Big Bang" (Unfinished Episode)
Obi-Wan and Grievous would have one more duel in The Clone Wars TV series, but this time as an unfinished episode. Released as part of The Clone Wars Legacy project, the "Crystal Crisis on Utapau" arc had Obi-Wan and Grievous face off in the form of a story reel. The two locked blades in the arc's final episode, where Obi-Wan and Anakin attempted to stop Grievous from obtaining a giant kyber crystal. This encounter is considered official Star Wars canon, despite the episode never being fully completed.
Grievous was once again able to beat Obi-Wan, this time much faster and ending with Obi-Wan's capture. However, Obi-Wan had also let go of some of his serious anger, asking Grievous to surrender and then joking about it when he himself was captured. With Anakin's help, Obi-Wan escaped and used the kyber crystal to destroy Grievous' ship. Obi-Wan even had a chance to give Grievous a friendly wave as he and Anakin were making their escape.
Star Wars: Episode III - Revenge of the Sith
Obi-Wan and Grievous would duel for the last time in Revenge of the Sith. Following the death of Count Dooku, Grievous returned to Utapau, where Obi-Wan tracked him down to finally put an end to the Clone Wars. Obi-Wan decided to return to his old approach, landing behind Grievous and giving the same "Hello there" that the droid general once had. Having seen what Obi-Wan could do when surrounded by droids, and wanting to finish the job himself, Grievous prepared to face Obi-Wan for the final time.
Obi-Wan was much more careful at the start of this duel, and his experience fighting Grievous paid off, cutting off two of the general's hands before disarming him completely with a powerful Force blast. Grievous attempted to escape again, but Obi-Wan was determined that the Clone Wars would end there, and the two engaged in hand-to-hand combat outside Grievous' ship. Obi-Wan was thrown off the edge of the platform, hanging on for dear life as Grievous closed in for the final blow. Grabbing Grievous's own blaster with the Force, Obi-Wan shot him repeatedly in the chest, killing the general in a burst of flame.
After years of fighting, Obi-Wan and General Grievous' rivalry finally came to an end. Grievous had tested Obi-Wan's spirit like few others, driving him to the point of anger and revenge, which could have pushed him to the dark side. In the end, however, Obi-Wan was able to remain a true Jedi, defeating his enemy out of self-defense and without being consumed by hate. Grievous, however, could never let go of his hatred for Kenobi and the Jedi Order, which eventually led to his own demise. Obi-Wan and Grievous fought many times in Star Wars canon, but like Kanan Jarrus would say, "It's not who's first. It's who's last."