As the Salvatore School prepares for its annual football game against Mystic Falls High, the latest monster to arrive in Mystic Falls sets its eyes on one of the students. Alaric goes head to head with Professor Vardemus.

When a samurai shows up looking for a demon that possesses its victims, Josie leads the charge to defend her friends from the demon's wrath; MG is conflicted by a secret he's uncovered about Lizzie's new vampire friend, Sebastian.

As the Salvatore School prepares for its upcoming ‘80s-themed decade dance, Hope and Lizzie find themselves trapped inside a never-ending labyrinth with a monster on their trail.

As the witches of the Salvatore School come together to celebrate Coven Day, the latest monster to infiltrate the school targets Alyssa Chang and the other students by spreading discord and creating chaos among the covens. Elsewhere, Alaric, Lizzie and Josie search for a solution that keeps Josie protected from the dark magic brewing inside the mora miserium. Fed up with feeling powerless alongside Hope, Landon asks her to give him self- defense training. Finally, Alaric's past comes back to haunt him.

After learning that Josie, Lizzie and Alaric are in trouble, Hope leads the charge to save them. Meanwhile, Landon seizes the chance to keep an eye on the latest monster in town in order to prove himself useful. Elsewhere, MG’s attempt at a perfect first date with Kym takes a disastrous turn when Hope enlists his help in her plan.

In a race to save Josie, Hope infiltrates her subconscious and finds herself in a fairytale world filled with dark magic. Back at the Salvatore School, Alaric, Lizzie and the Super Squad commit to their own risky plan to get Josie back despite the potential consequences.

In order to get a handle on some urgencies at the school, Alaric sends the students off-campus for their first-ever field day. But when a medieval monster arrives with a challenge, the students are left scrambling to guess which one of them may be a worthy opponent.

The students prepare to put on a musical about the founding of the Salvatore School at the behest of their mysterious new guidance counselor. Meanwhile, as Landon throws himself into writing the musical and Lizzie, Josie, Kaleb and Jed dive into their roles, Hope distances herself from the musical.

After a sudden mass exodus of the school's student body, Alaric and the squad desperately try to recruit new students to keep the school afloat. Hope agrees to help Lizzie with the new student orientation. Josie enjoys a fresh start on her first day at Mystic Falls High, while MG begins his semester of "no."

Lizzie suggests holding a fundraiser for the school. Cleo helps Hope cope with her emotions. MG seeks help from Alyssa. When a leprechaun shows up at the school, it might be what they need to turn their luck around.

MG finds himself on the outs with the Super Squad after a controversial decision he made comes to light. Hope puts a risky plan in motion regardless of the potential consequences. Kaleb, Cleo and Alaric join forces when the latest monster shows up.

Hope realizes she has a difficult choice to make, much to Alaric's disapproval; Kaleb and MG come up with their own plan to help Hope; Alaric realizes he needs to relinquish control.