Intro - this post's purpose is to describe & analyze all fights which took place between these 2 before ROTS. The continuities of both legends and canon shall be mixed in this post. But i will refuse to include the novel of ROTS or the movie version of their duel.
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Canon comic book's;
Chronology - since obi wans hair was long here this's before the battle of Christophsis/tcw season 1. Anakin was still his padawan here but he does not see or meet grievous.
Images;
Analysis: grievous relied on cheating immediately after the force push, though it appears he fought in a calm cool collected manner. Obi Wan left with the kid/hostage afterwards but never tried confirming the fate of grievous, this incident can be seen as obi wan overpowering him or in the best case a stalemate for grievous.
Detail's; Obi Wan had been captured prior to the fight itself, how exactly he was captured (by crook or hook) has not been elaborated upon.
This photo was for the conditions of obi wan before the fight, i wonder if it proves he was inferior to Grievous.
Their duel itself:
Analysis - The same old sloppy predictable, redundant script writing where a generic kick was done by grievous then he shows overconfidence by trash talk and falls for a force ability.
Based on later images obi wans hair was shorter in the comic book of this incident so its possible this was either after anakin was knighted or during anakin's last week as a padawan of the jedi order.
Other than these 2 incidents their was no comic book where they fought eachother unless you include the ROTS comic adaptation.
Image's;
Analysis: Here it would seem that grievous's unarmed combat skills were better than his abilities as a light saber duelist. Also unlike the movie here none of his arms/hands were cut, instead obi wan cuts his light saber hilts but not his wrists or fingers.
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Now to move on with their legacy of their rivalry, here i will focus on their engagements in the clone war tv series (2008) which i basically hate but still i will try to analyze them or show evidence of these conflicts.
Duel 1;
Basic's - On the planet saleucami, obi wan was looking for Grievous, but upon finding him they both engage in a super short duel which ended in a impasse. Grievous retreating can be excused due to the amount of clone officers nearby, it became a danger-zone (he may not be able to handle multiple clones with obi wan at the same time).
Obi Wan disarmed grievous of 1 blade hilt but Grievous kicked him in the abdomen sending him away.
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Conclusion - For many seconds obi wan was KOED so its fair to assume if their was no plot protection (or clone presence) Grievous could have slain obi wan here.
Kamino:
Basic's - here grievous actually did maintain the upper hand though again the writing team of the show opted for a generic script which led to grievous only getting a upper hand if he kicked his enemy.
They lacked creativity so they could not write it out to the point where grievous would use something besides his foot.
And once again his overconfidence/trash talk leads to grievous becoming vulnerable and failing in his objective. Cause obi wan uses a force push to make him run again.
Malevolence:
Basic's - here their fight did not appear to be a legit one cause they barely touched eachother, it was not a lengthy one either. All that happened is that obi wan evades the attack attempts of grievous then falls down due to losing his balance or being unaware of his own surroundings (whats in his back), after that he runs away. So its a inconclusive incident.
Rescuing Eeth Koth episode;
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Basic's - though grievous indeed choose to run away more than once still his kicks were able to push obi wan back by a considerable distance. Though i firmly believe obi wan had plot armor the actions done by grievous expose him as a coward here, he cheats by using his guards to team up on him.
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Grievous even staggered backwards after one slash maneuver of obi wan.
Battle while attempting to escape:
During that episodes ending their was one more duel between them it can be argued grievous could have won if escape was not a priority here. So he kind of redeems himself abit.
Season 5:
And the crystal crisis arc would be something i do not need to analyze or provide any evidence for because it has already been discussed and its a well known incident which proves that grievous defeated obi wan fairly their.
=Comparing them both (who won more often)?
In the magnaguard fight it was obi wan that did better so he gets a point for that, but while escaping grievous kicked him away so grievous got a point too.
Source - mission to rescue Eeth Koth episode
In season 5 its grievous who gets a point & kenobi gets nothing.
In the mission involving the wookie senator it was obi wan who performed better.
In kamino its basically a draw. Malevolence was inconclusive. So no points their.
At Caliban grievous failed, but he had to have captured him somehow off screen before caliban so both get a point here.
So far; 3 to 3, they're tied in points.
Crystal Crisis was grievous's W but Utapau in ROTS was kenobi's.
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