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Generally a Master and Servant participates in a Holy Grail War with the promise of a wish to be granted. in some cases like with Tokiomi Tohsaka and Waver Velvet the wish granting of the Holy Grail isn't their goal (the former sought the Root which is the main function of the grail, the latter just wanted to prove himself by winning) while other's like Diarmuid Ua Duibhne had their wish granted by being in the war.

However to my understanding with the Fuyuki Holy Grail Wars (Fate/Stay Night), the Moon Cell's Holy Grail War (Fate/Extra) and Tokyo Holy Grail War (Fate/Prototype) there has never been a victor and in later iterations something would actually prevent the proper granting of a wish (Fuyuki = Angra Mainyu's corruption. Moon Cell = Twice telling Masters to make his wish or be destroyed. Tokyo = Questionable if wish granting was ever possible, the true purpose was to summon Beast)

However i'm not entirely sure about some of the other Holy Grail Wars like the Subcategory Holy Grail Wars (Fate/Apocrypha, Fate/Labyrinth), the false Snowfield Holy Grail War (Fate/Strange Fake) or any other Holy Grail War i have missed as to whether or not they could and/or ended up granting someone's wish.

So has there ever been a Holy Grail War where the victor got their wish?

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Yes, one: the only Holy Grail War in the world of Fate/Grand Order, whose victor was the founder of Chaldea and its first director Marisbilly Animusphere with his Caster Servant,

Solomon.

As for what he wished for, it's not clear but Servant Sherlock Holmes (yes really) speculates in the Camelot chapter of the game that it was a wish for Chaldea, the work of his life, to succeed:

Sanzang:

Umm… Can I ask something? I’m not trying to complain that I’m tired of keeping quiet all this time, but… You said that Marisbilly guy got the Holy Grail, right? What did he wish for?

Holmes:

Unfortunately, Hermes has no record of his wish. It only shows the results. According to Hermes, Marisbilly flourished as a magus after the war. In the Clock Tower, Chaldea and the Animusphere family’s theories had heretofore been regarded as abstract and impractical. But, a string of successes reversed the Animusphere’s fortunes. The Heroic Spirit summoning system was established. Virtual experiments were conducted that allowed one to not only observe the future, but to interact with different time periods through rei-shifting. Around 2004, Chaldea, previously a mere astronomical observatory, was built into a research facility.

Conventional reasoning would conclude that Marisbilly wished for prosperity. He had no reason to wish for the incineration of the human order. According to documents, his personality was “hard-working.” He had ordinary desires, ordinary envy, and he loved ordinary fortune. That’s the kind of man he was.

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