OK, He won [url=http://www.bungie.net/7_Master-Chief-vs-WWII-Russia/en/Forum/Post?id=62164506#referred-OffTopic%20%28Offtopic%29]yesterday[/url] against WWII Russia.
So, now, he is facing off against the entire might of the United States.
The battleground with be the continental United States, Canada and Mexico. So all of North America. The cities are populated, and the entire military is home, including all hardware.
Chief has his Halo CE Magnum, and the Assault Rifle. He has reload boxes that are scattered about, but no two are closer than 5 miles apart, and he can only access them once every 6 hours. At them, he can switch out for a Shotgun, Sniper Rifle of Spartan Laser.
The US Military is at full strength, well rested, and fully equipped.
To win, Chief must be able to knock out enough of the leadership that the unit cohesion falls apart in the military. It has to be proven incapable of fighting him. For the military to win, they need kill or capture Chief.
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If Master Chief can fight through literally armies of Covenant, he's got this pretty easily