Janeway is a bipolar bitch. Picard would negotiate with her, and she’d go along with it because she respects him. Kirk would fuck her and afterwards, she’d flip out and attack him for it. But he’d still kill her.
I could get behind Kirk for the reason that Picard would waste time trying to negotiate with him, while Kirk would get right down to fighting. But the fight must take place at Vasquez Rocks.
Given how often Worf seems to get his ass handed to him, I don’t particularly hold Klingon combat skills in high regard. I mean, look at how extra-spikey their weapons are - to me, that says “overcompensating”.
I say Kirk (unless it came down to Karaoke, in which case, Brannigan wins and we all lose.)
They just like sharp things. From early childhood a Klingon parent will call to her children, “Quickly, run and see who can bring me the scissors most quickly!”
“Then stab your slower sibling with them as they are clearly lacking strength and honor.”
You are not of the body.
Remember the lesson of Mirror, Mirror. Thinker beats barbarian.
Rather, seducing the other guy’s Captain’s Woman wins. 
Did Data ever lose a fight?
Closest I can think of is in the First Contact movie where he’s captured by the Borg.
Kirk would win.
Even if his life depended on it, Picard couldn’t even flirt his way out of an retirement facility full of old ladies.
But neither of them have beards.
There was an altogether ridiculous moment in the “Reunification” episodes where a Romulan darts forward and yanks Data’s phaser from its holster.
Data’s “off” button has been hit several times against his will, by Riker, Lore and Crusher.
I can only assume you mean "These Are The Voyages" Kirk because that was the height of his badassery. Even then I’d have to go with Picard. While it’s true that Kirk is a card advantage machine, he is outclassed in both keyword power and stats pretty much across the board. He’s down by two points of cunning, two points of integrity, and the strength is equal.
Enjoy,
Steven
Why the rolling eyes?
Cant people who might be new to ST or the internet have thoughts?
Picard.
MiM
Here’s how I see the scenario playing out: The challenge is issued for a hand-to-hand fight to death. On the battlefield on the planet below, two cylinders of TV static materialize, and take humanoid form. Then, Worf proceeds to pummel Kirk into bloody oblivion.
Picard is smart enough to realize that he’s the friggin’ captain. Getting into fistfights isn’t his job; he’s got people for that.
Bah if you are going to use that theory, then Kirk would buy himself time by expending Red Shirts to tire the Klingon first. Then he would carefully start a rip in his shirt and charge in to take down the Klingon single handed. Somehow the log would never reflect that the Klingon was already injured before Kirk subdued him, but Kirk would win as always.
Meanwhile the mental might of Spock would be locked against the combined intellect of Data, Picard, Geordie and the Wesley. While they are still trying to design a system, Scotty of course finds a way to exploit an technological hole in the newer Enterprise as he wrote the Engineering texts that the shield technology was based upon.
In the End, Kirk wins because he had Spock and Scotty and they trump all other support characters.
Here’s the thing, Kirk doesn’t willingly expend crewmembers if he has the choice. He feels bad for every redshirt who dies (partially because he’s gone to the Academy with every one of their fathers, in the highly patronage-centric Starfleet of the 23rd Century).
Also, we have to consider the time period. If this is DS9 era (so, from the end of TNG to about 6 or 7 years after), then the Enterprise (registry NCC-1701-no-bloody-a-b-c-or-d) doesn’t have enough redshirts to tire Worf out before he gets to the main attraction. On TNG, he exists to show how tough other guys are. On DS9, Worf is fucking epic. We’re talking about the kind of guy who gets epic poems and operas written about him by the very people he kills.
Scotty wins over Geordi (there was a TNG ep devoted to this very concept), but O’Brien can out-do Scotty in a combat situation, because he’s not only got the skill and the British Colonial Charm, but he’s a battle-hardened veteran of two brutal wars and knows how to apply his engineering skills on the battlefield.
Data and Spock would try to outlogic each other, then sit down for a relaxing 85 hour game of 3D Chess or Strategema. Similarly, Scotty would just get distracted by the pure joy of taking Data to a bar, if it’s post-emotion chip. Pre-emotion-chip, Scotty will have no interest in the dull android.
This is why Sisko wins.
Er… how does that work, exactly? Sort of like Sir Robin and his favorite minstrel?
"I had to kill him, Captain; honor demanded it. He wrote the epic poem " ‘Rime of the Security Chief Who Couldn’t Shoot Straight.’ "
He was captured by Lore and Co. as well as the collector guy.
“Ladies…Ladies, Please! If you would just…May I have your attention? If I may…”