FROM: Zork series/Pong
The Pong paddle is on a pitch-dark field. It is likely to be eaten by a grue. After the paddle fails to heed several warnings to turn on a light, a grue approaches and attempts to eat the paddle. However, the paddle is too big to go down in one gulp, and because it's made out of pixels - as opposed to pure imagination, like the grue - the grue has a hard time trying to bite off a piece. It isn't long before the paddle gets lodged in the grue's throat and the grue chokes to death. Pong Paddle wins.
FROM: Mr. Driller/Zero Wing
Oh, God, these two? This fight has been canceled due to total lack of interest. Crash Bandicoot wins.
FROM: Mega Man series/Street Fighter Alpha series
After savagely beating Dan into near-unconsciousness, Mega Man tries to do what he does at the end of every major fight: steal his enemy's power. However, Dan has zero power. Mega Man's robot brain tries to divide by zero and explodes. Dan cheers his own mighty prowess.
FROM: Monkey Island series/Legend of Zelda series
Guybrush attempts to engage Link in the time-honored art of Insult Swordfighting, but finds himself thrown off when Link only responds to his insults with "HUP!" or "HAAAAAAAAH!" Confused, Guybrush starts clicking things in his inventory on other things, and Link has a sudden, violent flashback to the time when the bad men came and made him do the bad things on the CD-based system with the awful point-and-click interface. Overwhelmed by trauma, Link slips into a fugue state and goes blood simple.
When the red haze in front of his eyes finally clears, Guybrush is lying in several ragged pieces at his feet. Horrified, Link tears off his evidence-soaked clothes, stuffs them into an incinerator and silently vows never to speak of this (or anything else) again. Link wins.