Blue. Caboose has the highest Kill count next to Doc. Griff (Red Vs Blue) vs Homer in a Donut eating contest.
I'd have to go with the spy, if you're looking at the meet the spy vid. Cole from Infamous vs Kennen from League of Legends.
The backwater peasant oddly enough, right up to when the West and Japan intervened A massive, heavily armored champion of a soldier who had fought in dozens of battles vs some kid with a sling
Realistically, the warrior. Yeah, I know the story, but that was either a damn lucky shot, or Goliath was so overconfident that he left himself open. The best soldiers the Galactic Empire had left vs a bunch of *squee!*ING TEDDY BEARS WITH STICKS AND ROCKS.
Seeing as most Imperial Stormtroopers couldn't hit a brick wall at point-blank range, the teddy bears (with a little help from the Rebellion) win this one. The mighty British Empire at its height with then-top-of-the-line weaponry versus a bunch of drunk (and probably stoned too) farmers and merchants with outdated hunting equipment.
The bunch of drunk farmers and merchants, albeit with French money and top of the line rifles A god vs a nonbeliever
God. The British Army, led by some of it's finest commanders and is extremely well equipped vs. A bunch of drunken illiterate militamen armed with farming equipment.
Morph did that one already.... I really don't see the point of these history ones. Anyway. Deadpool vs G1 Cartoon Starscream.
Deadpool. If Rainbow Dash can beat ol' Screamer, I don't see why the Merc with a Mouth couldn't. G1 Grimlock vs. MMPR Tyrannosaurus Zord
While I don't like back and forthing, I had to answer this one. Grimlock. The Zord may be larger, but Grimlock is far more maneuverable. The Zord are meant to monsters about their own size. Grimlock may be dumb in the G1 cartoon, but he'd taken on larger opponents and won. If we're talking comic Grimlock, he got an eight rating intelegence. Eight out of ten, he plays dumb to make his enemies underestimate him. He'd have no problem coming up with a plan to stop even the Megazord let alone a single Zord. Matt Tracker (M.A.S.K.) vs Michel Knight (Knight Rider)
The bear. Doesn't matter the size no dog is going to beat a pack of bear. Woder Woman (DC Superhero Girls) Vs Starfire (Teen Titans Go)