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Dio is fast enough to catch Gate of Babylon's swords (like Berserker did in Fate/Zero), and time stopping would probably be enough to kill Gilgamesh. Well, at least F/SN and F/Z Gilgamesh, I don't know anything about Fate/Extra, but being MFTL+ he could easily blitz Dio before he can use The World's power and destroy his head.
 
Well, Fate/Extra is an annihilation.

Gilgamesh has resistance to time stop. so, Fate/Stay Nigh is inconcluive.
 
Fate Extra one is an overkill.

Fate Zero or Stay Night Gilgamesh hits Dio with Gae Bolg and one-shots him. Dio lacks durability and destructive capability.
 
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