Oh, this really is quite the intriguing topic. The elder Darth Tyranus versus the young Darth Vader-to-be. Whoever manages to prevail, we know it'll be spectacular. We've never truly seen Dooku tap fully into his skillset, save against the venerable Master Yoda. As far as the combatants in question here, television and the films seem to bounce all over the place when it comes to them.
Their first bout was well-balanced indeed -- an extended, practically equal exchange that ended when Dooku landed a lightsaber swing to Anakin's arm:
Their rematch on Tatooine in the TCW film functions well as a progression of their previous standing -- like before, Dooku and Anakin battle for a good amount of time, almost even, and then Dooku lands a blow. Because Anakin is stronger, the blow is less decisive -- a Force blast, as it happens:
The trouble is, the film seems to ignore Episode II, as Dooku claims that Anakin's training has "come a long way". A shame, really, for the two duels fit so well together in terms of forwarding the narrative of Anakin gradually growing stronger and stronger against Dooku.
In anycase, Dooku and Anakin cross swords again much later on in the show. They appear relatively equal, with Anakin's superior physical strength making itself known:
However, Dooku still maintains a noticeable edge in sheer power, for he dominates Anakin in that encounter thereby:
It's their second confrontation on Naboo where, I do believe, the showrunners make the transition, more or less, to peak Anakin. As strong as he had become in their last fight, his connection to the Force is considerably stronger now -- evidenced by how he handles a strike from an electrostaff in each encounter. Not to mention, his superhuman strength hardpressing Dooku's telekinesis:
When they engage in lightsaber combat, it is Anakin who holds the upper hand. He seems to drive Dooku backwards, and after a bit, lands a blow of his own. It's a kick, and when Dooku is forced to the stairs, Anakin presses his advantage and begins to physically choke him:
And I do think this is where many fans tend to forget what happens. Put plainly: Dooku wins.
Anakin gets the upper hand, but Dooku forces him off, and achieves a follow-up temporary incapacitation. It is made clear nevertheless that Dooku has been pushed to dig more deeply into his own abilities than ever before in his various fencing matches with the young "Jedi".
The writing of TCW already ignored the Episode III lines regarding Dooku and Anakin having not clashed since Geonosis, so it strikes me as odd to assume that TCW would view anything else in that very same sentence as binding. Namely, Anakin's powers having doubled. Their second Naboo brawl generally marking the entrance of Episode III Anakin is further reinforced by the fact that when the TCW team got a chance to write their own version of a final showdown between Dooku and Anakin, the former lasted about as long as he did on Naboo:
Anakin is stronger than ever, and so the blow he eventually lands is upgraded from a kick to a cut. Likewise, Dooku is unable to turn the tables in this encounter, as he managed beforehand. It is a curious reversal of the Episode II and TCW film fights. In fact, were we to disregard Dooku's statement on Anakin's training having significantly improved -- or better yet, attribute it to Anakin's newfound ability to handle Force Lightning -- an exceptionally streamlined sequence of progress is created.
All of the dueling matches between Dooku and Anakin are extended, by all appearances tough. In the first, Dooku eventually lands a lightsaber blow. In the second, Dooku eventually lands a Force blast. In the third, no blows are landed. In the fourth, they tag each other equally, however Anakin lands his kick in more impressive fashion. In the fifth, Anakin eventually lands a lightsaber blow. Dooku begins ahead, but his lead decreases with time, evens out, and slowly reverses.
The issues now would be their other match in season 6, as well as Episode III. Having himself a good time, if anything, Dooku holds the upper hand over Anakin and Obi-Wan Kenobi simultaneously:
The Episode III duel tends to portray Dooku favourably over Anakin outright, taking into account the surrounding behind-the-scenes material. For the Oba Diah spat, however, we've been graced with no explanation. Perhaps Obi-Wan's presence prevented Anakin from cutting loose with his anger and hatred, and so we really see his Jedi skills pitted against Dooku here? Simply, the difference between Jedi Anakin and emotional Anakin? It's just speculation. It didn't work that way in Episode III, but then, the storytelling situation is a little different.
I believe that if you take into account TCW as a whole, Dooku would generally lose to season 6-7/Episode III all-out Anakin. He would always take Jedi Anakin. Looking at Episode II, Anakin with further improvement should at least be Dooku's equal by the end of it all. Looking at Episode III, Dooku should beat Anakin whether or not the latter is exercising Jedi restraint.
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