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I'll go step by step.


Star Destroyer vs Enterprise

Outside of fanboy love for one side or another, who wins largely relies on whether you believe in stat books or in "feats".

Example, you see two ships attempt to accomplish the same vital feat. One of them succeeds, and the other fails, however the stat books say the other has the more powerful weapons.


Star Wars has a much more impressive "technical loadout" however Star Trek the enterprise actually has better "feats".

If you're a stats book person, the Enterprise shouldn't be able to even hurt a star destroyer.

If you're a feats person, the star destroyer shouldn't be able to hit the enterprise, and will be picked apart by the much smaller ship.