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Like the Bride said, the details of her story tend to change depending on who's telling them.

It turns out Duncan and Conner were there! They weren't members of Bill's group per say, but they owed him a favor, and The Bride "is" as much of a killer as the people who crashed her wedding rehearsal. And Bill can be very persuasive..

Bride has no idea they're Immortals, or that the only way to kill them is by taking their heads.

She goes after Duncan first. If she wins, she goes after Conner next. If she kills them both, they get resurrected, and she has to face the team. If she wins that, she has to fight every Immortal the two ever faced, all at the same time. (Bill can be VERY persuasive.)

This fight happens at the same arena she faced the Crazy 88 in.

And if she survives, she wins.

In anticipation for calls of "spite", as I've seen fights on forums go to Duncan when it's 1 vs 1, I'll just say:

Bride may as well be Immortal, considering she survived being shot through the head, through the chest, slashed in the back, and came back from fatal injuries all the time. She can take about as much abuse as any Immortal's taken, imo.

She's crazy strong. She lops through thick bone in one swipe, and even cut a guy in half. She impaled a guy, lifted him up from the hilt, and tossed him. She punched through that casket, against six feet of dirt weighing it down, and dug herself out. You need to decap a Highlander to kill them, but to my knowledge they've never regrown limbs or from being severed in two..

She's fast. Almost super humanly fast.. If Duncan or Connor have high end feats, they're pretty rare, because as I recall they were roughly human level...

Duncan destroys her!

If you discount the fact that he achieved speed blitz feats at the end of the saga...fair enough.

He was there whilst styles of martial arts and sword styles where being invented.
He defeated a skilled sword fighter in a room in total darkness whilst the opponent wore night vision goggles.

He defeats her without much problem. Conner laughs from a distance.

this is playing as Duncan beheads her..

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Bride wins.

Duncan wins.

In a normal fight I'd side with the Bride. In a situation where she needs a very specific fatal strike? The chances of the Immortals taking her down increase due to this.

Highlanders have decades of skill behind them and are immortal. They know their immortal and can take a thrust to the torso to take her head. Beheading is something they aim to do in fights since they mostly prepare themselves to fight other immortals so I'm sure she will loose her head.