18 - 8 is already a lopsided head to head. And 6 out of those 8 wins were not against the best version of Kim but against a weakened/distracted Kim. Then there was a good win for Shego vs Kim in ASIT but ASIT is a deleted timeline, which means that win doesnt count. So in the end, the only good win against Kim that Shego has had is from the Ron Millionaire episode.

And now here are the 18 times where Kim prevails against Shego

Season 1

Crush - Kim using a weapon (KO Gas) against Shego

https://i.redd.it/v49e1fkbjwee1.gif

Kim used the grappling gun to entangle the robot's two legs, which then caused the robot to trip and fall and forced Shego who was inside of it to quickly jump out and grab onto a very high horizontal steel beam, from which she could not find an easy way down to the ground.

https://reddit.com/link/1i8sj8i/video/mgtd40jxywee1/player

Tick Tick Tick - Kim exploiting Shego's missed kick

https://i.redd.it/fyvq0bpfowee1.gif

Bueno Nacho - Shego did not anticipate an energy beam coming between her and Kim and destroying the platform that Shego was standing on and thus ended up falling down to the ground floor that was flooded with melted cheese. In contrast, Kim had already anticipated that the energy beam would destroy the platform that she was standing on and thus pulled out her grappling gun at the right time and then used it to swing her way to an exit.

https://reddit.com/link/1i8sj8i/video/32huy972zwee1/player

October 31st - Kim overpowering Shego

https://i.redd.it/ipt7l5hsowee1.gif

Season 2

Naked Genius - Kim using a weapon (adhesive-shooting gadget) against Shego

https://i.redd.it/tl6e96kwowee1.gif

Two To Tutor - Kim absorbing the momentum from the mixer and then using all that momentum to land a kick onto Shego

https://reddit.com/link/1i8sj8i/video/v2krozerzwee1/player

Adventures In Rufus Sitting - Kim trapping her foes in a parachute

https://i.redd.it/e6nl6n4z0xee1.gif

Rufus vs Commondore Puddle - Kim exploits Shego's missed swipe by kicking her toward a downward slope before Shego can do another swipe against Kim

https://i.redd.it/g7dm8e57swee1.gif

ASIT - Shego's bad luck of having a lamp post bounce off a mattress and then fall down onto her

https://i.redd.it/2vdsq2p1xwee1.gif

Blush - Kim putting a tablecloth over Shego's head to temporarily blind her

https://i.redd.it/kpxjvbr5xwee1.gif

Truth Hurts - Kim creating distance between her and Shego and then making the ice sheet underneath Shego collapse

https://i.redd.it/w9131yo7xwee1.gif

Ron Millionaire - Kim exploiting Shego's late jump

https://i.redd.it/81j4bbr1ywee1.gif

Season 3

Bad Boy - Kim exploiting Shego's missed kick

https://i.redd.it/fm72ur7czwee1.gif

Rappin' Drakken - Kim closing the door to block Shego's view of Kim's body and then discharging a large amount of mind control liquid from a shampoo bottle onto Shego's face

https://i.redd.it/mzrtn95ezwee1.gif

STD - Kim using a weapon (superspeed punches from her battle suit) against Shego

https://i.redd.it/7rbj4lm00xee1.gif

Kim using a weapon (superkick from her battle suit) against Shego

https://reddit.com/link/1i8sj8i/video/c6p0jfpf0xee1/player

Season 4

Clothes Minded - Kim performed a new countermove that Shego did not anticipate and got completely surprised by the move

(click on the link to see the gif) https://i.postimg.cc/Qx16cZK9/S4-E8-Clothes-Minded.gif

Overall, Kim wins most of her fights against Shego thanks to her speed, agility, and reflexes to dodge Shego's glow blasts and to dodge & block Shego's physical strikes, her expertise in counter techniques, her creativity in devising new countermoves and her resourcefulness with her gadgets and the elements in her surroundings.

Madison Howard

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Spiritual-Doctor1973

The head-to-head between Kim & Shego