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Early into Fate/Stay Night, there is a scene where Shirou sees Sakura and another man:

Gilgamesh and Sakura

In the Unlimited Blade Works Route, we confirm this other man is Gilgamesh. When Sakura talks to Shirou, she says that the other man was a foreigner and she couldn't understand him. However, we can see from the image that that may not be the case.

Since Gilgamesh has been tainted by Angra Mainyu's corruption of the Holy Grail from the previous war, and Sakura is a "Black Grail" Vessel with a deeper connection to Angra Mainyu than the "White Grail" Vessel (Ilya), did Gilgamesh already know about Sakura?

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  • There is no definite answer to that I guess. You can assume that he did, or that he just sensed her connection to the magi world/her being a master.
    – Uriziel
    Commented Jan 31, 2014 at 14:06

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To complement Anon153's answer, here's a relevant quotation from TYPE-MOON Wiki:

Gilgamesh is one of the antagonists in each scenario of Fate/stay night. He first appears before the start of the Fifth Holy Grail War around Sakura's house. He identifies her as “the other Grail” and comes to tell her “Go die right now.” It is just a suggestion rather than a command, as he believes that the matter will develop into some sort of entertainment regardless of the situation. When questioned about the encounter, Sakura just claims that he was asking for directions and that “It was English” in order to hide the truth.

And source referenced is as follows (Citation Note 14):

Fate/complete material III World material - FAQ with Nasu: General Questions about Fate, p.130
Q: Prior to the start of the Holy Grail War, what was Gilgamesh doing around Sakura’s house?

A: Yes. He came to tell Sakura to “Go die right now”. It is rather a suggestion than command. Regardless the situation, from the King’s perspective, this matter will develop into some sort of entertainment. As a result, what Gilgamesh said was not a command. Sakura’s reply “It was English” was a convenient excuse to hide the truth.

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He knows that Sakura is "the other grail" besides Illya, thus he approach/come to her and said "Die" to Sakura, because she is the "fake" grail. And, Gilgamesh can't be tainted because of his high ego

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    Actually he can, unlike Alter-Saber and Blind-Berserker it's Gilgimesh's ego which prevents him from falling too much and the taint really just amplifies that ego. I also remember it saying his class skill was unnaturally boosted by the Grail's taint
    – Memor-X
    Commented Aug 29, 2014 at 13:18

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