This is a hard one. My initial feeling was that Conan and Red Sonja take it through stats and durability, and fairly equivalent skill. I’m not hugely knowledgeable on Conan, but that’s my impression anyway.
But DD and Elektra are both very agile, and could use the scenery to their advantage, especially when starting at this distance. Should they choose to, they could go to ground and then used DD's senses to track their opponents and attack from cover.
Plus, DD and Elektra are both pretty good damage-soakers themselves. In Elektra's last issue, she was beaten down to the ground with a brain hemorrhage, fractured skull that later required reconstruction, and was blind in one eye. Then the next page she managed to get up and full-on blitz two leader-priests of the Hand and Bullseye as if nothing had happened to her. A few issues before that she intentionally took a sword in the gut and twisted so it missed everything important, then went ahead and got into some more fights immediately after that with no problem.
They're also both very good at nerve strikes, whereas I'm not aware of Conan or Sonja doing that.
The weakness of the Marvel team is probably their weapons. Elektra normally has a sai, which have a short reach, and some shuriken. She can throw them all, so she can good ranged attacks, but up close she's lacking in reach. She is pretty lethal with even her bare hand though, having punched through people on multiple occasions. DD also can do ranged attacks but typically has a short reach with his billy clubs, unless he connects them as a staff. And he can't really parry against Conan's sword, I would think the sword would splinter the staff. More importantly as a weakness, they're just blunt instruments and won't be able to do as much lasting damage against Conan as Conan's sword could do against DD.
When I think of DD, I tend to think of him fighting skill-based opponents, not bruisers, but then we have a good example in Bruiser himself, who could presumably hit even harder than Conan, although he is probably less skilled. Other fights against strong characters might include Sabretooth, Kingpin, Captain America, or Spider-Man. Thinking about them gives me more hope for DD than I was initially thinking. The recent BotW with DD vs Bane is semi-similar.
Sonja should have better stats than Elektra but I am guessing Elektra has more skill, and possibly reaction time, having cut a bullet in half, and in terms of agility, run along the edge of a sword while it was in mid-air being thrown at her. Sonja has a healing factor but not enough to help her if seriously wounded. If it was a year or two ago, I don't think Elektra would have much of a chance, but her recent series has given her a lot of wins over some pretty good superhuman foes. Plus, she took out a squad of SHIELD agents with paintball guns! :)
Anyway I am sort of arguing myself into thinking that DD and Elektra start off as underdogs, and go for the nerve strikes for the win.
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