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Chell gets the portal gun, and a loyal companion cube.

Freeman gets the gravity gun.


The arena is a test chamber littered with obstacles, portalable surfaces, refractible lasers, buzzsaws, gas barrels, and loose stuff to throw around, death drops into bottomless pits and incineration chambers. And GLaDOS is "officiating", e.g. actively messing with them while keeping is sporting for her amusement.

Freeman and Chell start on opposite ends of this course.

Who wins?

Chell. She's got the advantage in maneuverability with portal gun and acrobatics she displays in one of the Portal cinematic trailers. She's going to keep making Gordon fire barrel after barrel, cube after cube at her 'til he runs out of things to shoot with his gravity gun. Afterword, he's going to regret not finding a helmet to go with his HEV suit as Chell will deliver a high velocity kick to the face.