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Ciel si iscrive al prestigioso Weston College in seguito a una richiesta della regina di indagare sulla scomparsa di diversi studenti, tra cui Derrick Arden, figlio del cugino della regina.

Ciel's efforts to earn praise from his peers with Sebastian's help bring him the attention of the four prefects, who invite him for tea. Edgar Redmond, Scarlet Fox's prefect, sends his student assistant Maurice Cole, to deliver the invitation, but Maurice purposely gives Ciel the wrong time, causing him to be late. This leads to him being shunned by the prefects. Ciel and Sebastian investigate Maurice and discover that he pushes most of his assistant duties to his underclassmen, among other misdeeds. Ciel decides that he needs to infiltrate a spy into the Scarlet Fox Dorm. He convinces Soma to enroll in Weston College and take on the role.

Soma not only catches Maurice sending out task cards to underclassmen but also uncovers his other secret. In the art room, Ciel confronts him about his misdeeds and Maurice calls in his lackeys to attack him. Green Lion's prefect, Herman Greenhill, and his student assistant, Edward Midford, stop them. Ciel had attached strings to the paintings and connected them to gramophones at the Swan Gazebo, the prefects' meeting place. Thus, the prefects heard everything, and Edgar relieves Maurice of his position. Ciel also reveals Maurice's other secret to the school, spreading photos of his true appearance that he hides with makeup to be "the prettiest boy in school." Having uncovered the truth about Maurice, Ciel gains the prefects' favor and becomes assistant to Clayton, the Sapphire Owl prefect's assistant.

Having joined the prefects' social circle, Ciel inquires about Derrick. Their reaction makes him and Sebastian suspect that they're hiding something about his disappearance. Edward, the brother of Elizabeth, Ciel's betrothed, figures that Ciel is really here as the Queen's watchdog, not a student. Ciel and Sebastian learn from the other students that Derrick and a few other students were suddenly transferred to the Violet Wolf dorm six months ago by the principal. Out of options, Ciel and Sebastian cause a fire at Violet Wolf's dorm to force the students to evacuate, hoping to draw Derrick out.

The students evacuate Violet Wolf's dorm but neither Derrick nor the other missing students are among them; they were never at the dorm to begin with. Looking for another way to reach the principal, Ciel learns that every year, the principal invites the most distinguished student from the upcoming annual cricket tournament to the special midnight tea meeting. Sebastian arranges for Ciel to join Sapphire Owl's cricket team. During the opening ceremony, Ciel meets Elizabeth and her parents. Her father, Alexis, reminisces that Sapphire Owl won the tournament only once, back when he was a student. It is revealed that during that time, Sapphire Owl's prefect was none other than Ciel's father, Vincent Phantomhive.

Dietrich, a German exchange student and Green Lion's prefect, had lost a bet to Vincent after Sapphire Owl won the Cricket tournament. Having lost, Dietrich is asked by Vincent to be his subordinate for life, leaving him sputtering. In the present, Sapphire Owl's first match is against Scarlet Fox, who forfeits due to food poisoning caused by Sebastian. Sapphire Owl makes it to the final match against Green Lion, managing to always hit the ball thanks to Sebastian sending musical signals through the orchestra he is leading. Just then, the principal finally arrives to watch the match, causing a commotion. Sebastian rushes to capture him in order to inquire about the missing students.

With Sebastian absent, the Sapphire Owl team resorts to their other underhanded tactics devised by Ciel as backups. Sebastian keeps looking for the principal, but fails, as he is always one step ahead. When he drops all pretenses and attacks, the principal vanishes before his eyes, making the demon realize that they are not dealing with a human. Green Lion keeps behind Sapphire Owl in the score but closes the gap near the end of the game. In the last throw, Ciel puts himself in harm's way to distract Herman and seize victory, repeating his father's feat of having Sapphire Owl win the Cricket tournament.

After the match, Saphire Owl's team participates in the annual boat parade for the winners, though, due to their lack of training, they fall into the river during their greeting to the Queen. Ciel learns that he's been invited to the midnight tea that night with the principal for his efforts in the tournament. During the occasion, he confronts the principal and the prefects about the disappearance of Derrick and the other students. Agares states that won't be necessary as Derrick is here; sure enough, Derrick arrives, much to Ciel's surprise.

Derrick attacks Herman, taking a bite out of his arm, and Ciel summons Sebastian to restrain him. He realizes that Derrick was transformed into a reanimated corpse like those they faced aboard the Campania. The principal reveals himself as Undertaker in disguise, affirming that he'd been toying with Ciel and Sebastian. The four prefects confess that Herman killed Derrick months ago and they sought help from the Aurora Society to cover it up. Derrick, who was Redmond's assistant at the time, was assigned to investigate complaints of bullying occurring in the school, only for the prefects to discover that Derrick himself, along with four of his friends, were the culprits, tormenting and assaulting their schoolmates.

Despite witnessing Derrick's bullying, Agares had covered for him and threatened the prefects instead. Enraged at this, Herman killed Derrick and his accomplices, while the other prefects helped him cover it up, enlisting the help of the Aurora Society. Undertaker took this opportunity to continue his research and improve the corpses he creates. The Agares before them now is also a reanimated corpse; Undertaker's most successful one yet. Ciel orders Sebastian to capture Undertaker as they are attacked by the other reanimated students. Realizing that Undertaker's objective is to kidnap Ciel, Sebastian refuses his order and prioritizes protecting him instead, forcing Undertaker to flee. To prevent Derrick's crimes from being exposed and causing a family scandal, the Queen simply has the prefects expelled from Weston instead of arrested, with Edward and the other assistants replacing them as the new prefects. Ciel and Sebastian return home while the Queen considers welcoming Undertaker and his corpses as allies to England.

Soma and Agni visit Ciel. Ciel and Sebastian take the Phantomhive servants to London for some shopping. There, they analyze Undertaker's funeral lockets and discover the locket of Ciel's grandmother, Claudia Phantomhive, among them, making them realize that Undertaker has been associated with the Phantomhives long before Ciel and his father. While inspecting the sales of the Funtom Company's new line of perfumes, Sebastian saves Irene Diaz from an accident and escorts her to her opera performance in time. In return, she helps promote the perfumes, making them sell out. Ciel then hires Irene as the face of his products. Meanwhile in Germany, two hunters pursue a fox into a forest said to be haunted. They ignore the warning that they will be cursed and come across a giant wolf creature.