Fate/Stay Night depicts the Fifth Holy Grail War, in which seven masters each gain a heroic spirit as a servant and fight other masters to claim the Holy Grail, which can fulfill anyone's wish. The protagonist of the story, Shirou Emiya, is a reluctant participant who doesn't want to do anything with the grail. Still, he gains his resolve and fights to prevent the grail from falling into the hands of vile people.

Shirou's concerns aren't unfounded. An article of great power like the grail attracts people who would use it for selfish gains and their own goals, which often disregard the lives of others, if not outright harm them. Across his journey and the three routes, Shirou fights multiple antagonists, who threaten him or those he loves.

8 Medusa

A Loyal Servant To Shirou's Enemies

Medusa from Fate series

Medusa is a rider-class servant who was summoned during the Holy Grail War, serving Shinji Matou and later Sakura Matou, depending on the route. She is a skilled fighter who challenges Saber and goes toe-to-toe with her. Despite not being evil, Medusa is most often an enemy of Shirou.

The conflict with Medusa ends in different ways, depending on the route. In Fate, she is defeated after a prolonged battle with the Saber because the latter uses her noble phantasm. In Heaven's Feel, she becomes a protagonist and teams up with Shirou to save her master, Sakura, from the depths of despair.

7 Medea

The Ancient Spirit Devoted To Her Master

Medea smiling as she makes her debut in Fate/Stay Night: Unlimited Bladeworks
Medea smiling as she makes her debut in Fate/Stay Night: Unlimited Bladeworks

Like Medusa, Medea is not an evil person at her core. She is loyal to her master, Souichirou Kuzuki, whom she feels deeply in love with, and their devotion to each other is unquestionable. However, as a servant, Medea still has to fight in the holy grail war, and multiple times, she challenges both Shirou and Saber.

One of Medea's most notable acts is kidnapping Sakura Matou, causing Shirou and Rin to go after her. This shows that while Medea is protective and loving towards some people, she is willing to make sacrifices. She proves herself to be a challenge for the heroes before she is killed by Gilgamesh.

6 Dark Saber

A Twisted Reflection Of Saber

Artoria in FateStay Night

Usually, Saber, also known as Artoria Pendragon, is as far from being a villain as one can be. She is a noble, selfless person who fights both for the ideals of justice and the people she protects. However, a notable exception to this is the Heaven's Feel route, in which Saber's story takes a dark turn.

Shirou loses Saber in the middle of the war, and when she returns, she is subjugated and enslaved by Sakura Matou, who turns her into a dark version of herself. Dark Saber is a paperless enforcer for the corrupted Sakura and has no qualms about going against her former friends, which leads to an encounter with Shirou.

5 Shinji Matou

A Jealous Magus With A Twisted Streak

matou shinji

Shinji Matou serves as an antagonist in all three routes, but the degree to which he is important varies, as does how much the viewers learn about him. Shinji is the original master of the rider and tries to prove himself to his grandfather, Zouken. Zouken sees Shinji as a failure and a weakling, causing him to grow bitter and envious.

In the Fate route, Shinji is a brash and arrogant master who opposes Shirou, but the other two routes unveil the depths of his depravity. In Unlimited Blade Works, Shinji allies with Gilgamesh and is willing to violate Rin, while in Heaven's Feel, he is revealed to have done the same to Sakura, making him a detestable villain.

4 Sakura Matou

A Tormented Soul Lashing Out

Sakura Matou from Fate anime

Like Saber, Sakura isn't an antagonist most of the time. She is a good and supportive friend to Shirou, but she doesn't get much time to shine outside of her route, Heaven's Feel. That route reveals traumatic elements of her past and the abuse Sakura endured from Zouken and Shinji, which caused her to cling to Shirou's love.

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Much of the damage comes from the Shadow, which is spawned from Sakura's subconscious. She has no control over it, but after killing Shinji, she fuses with it and becomes Dark Sakura, who wants to bring her wrath to the world after enduring a lot of torment. However, her time as a villain is short, as Sakura thankfully breaks free from the darkness.

3 Zouken Matou

An Immortal Monster of a Mage

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Zouken Matou

Many of Shinji's and Sakura's crimes can be traced back to how they were treated by Zouken Matou, a mage who has sustained himself for many years and seeks immortality above all. Zouken saw both children as tools to use and discard, showing himself as a selfish and sadistic person who doesn't care for others. He uses unique Mato magecraft to keep himself alive.

He is mostly active in the Heaven's Feel route, where he partakes in battles and tries to manipulate Shirou into going against Sakura, serving as the overarching antagonist. Eventually, however, Zouken finally gets destroyed, and the world is freed from his manipulations and acts.

2 Kirei Kotomine

The Manipulative Sociopath

kirei-kotomine

Kirei is the major antagonist of Fate/Stay Night and is present in all three routes. He was acquainted with Shirou's adoptive father, Kiritsugu Emiya, whom he fought in the previous Holy Grail War. He is incapable of gleaning joy and satisfaction from most things, with the suffering of others being his main source of fulfillment.

In Stay Night, Kotomine manipulates Shirou into joining the Holy Grail War, taking an interest in the boy due to his relationship with Kiritsugu. He ends up either being a powerful enemy for Shirou to battle, or a reluctant and temporary ally in the Heaven's Feel route, but in the end, he meets his demise one way or the other.

1 Gilgamesh

The Cruel, Brutal King Of Heroes

Gilgamesh from Fate series

Gilgamesh is a twisted villain in the Fate route who goes on to become one of the main antagonists in Unlimited Blade Works. He is the servant who has stayed behind since the Fourth Holy Grail war and is allied with Kirei Kotomine. He is usually shown to be Saber's main antagonist, who Saber battles at the end of her journey.

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Gilgamesh is among the strongest servants and puts fear into the hearts of other characters. He is also arrogant and ruthless, claiming ownership of Saber, and has no qualms about brutally killing his opponents. Although he is an evil person, he possesses a lot of charisma, which makes him one of the most memorable villains in Stay Night.

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Release Date
January 7, 2006
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