Lainey returns to William Penn Academy as the new music teacher. Lainey has a hard time adjusting to being an authority figure, but she realizes she might not be so bad at it when she discovers a kindred spirit in Principal Glascott’s niece, Felicia. Meanwhile, Coach Mellor struggles with Michael Jordan’s influence on modern-day basketball.

Hoping to gain respect among her colleagues at school, Lainey comes up with a misguided plan to give an awkward and insecure student a full makeover. Meanwhile, Principal Glascott and Coach Mellor take friendly competition to a new level when they are both romantically interested in the math teacher.

Coach Mellor is cracking down on cheating, which leads him to take on the failing mathletes for the upcoming Math Olympiad. Meanwhile, Lainey helps CB deal with a challenging student.

After Mellor tells Lainey that sports are king at William Penn, she sets out to put on the Broadway hit musical “Rent” to show Mellor the arts are just as important as athletics. Meanwhile, Glascott and CB struggle to modernize the school’s outdated boy’s health education program.

When Lainey starts to teach the easy A course for jocks, Coach Mellor challenges her to expect more from his athletes. After CB points out Felicia needs to beef up her resume for college, Glascott bribes his niece to run for class president.

After two students show up to school dressed in backward clothes, a la Kris Kross, Lainey tries to get kids to conform to social norms to protect them from ridicule while CB encourages them to embrace their uniqueness. Meanwhile, Principal Glascott struggles to say no to his teachers and disappointing his friends, so he enlists the help of Mellor to lay down the law.

When her high school reunion is held at William Penn, Lainey tries to hide her teaching job from old classmates, pulling a “Romy and Michele” lie with the help of Erica Goldberg and CB. Meanwhile, Mellor’s distraught to learn his star athlete alum, Ruben Amaro Jr., sees Glascott as more of a mentor than Mellor.

As the new cheer coach, Lainey wants to bring the William Penn cheer team into the competitive competitions of the 90s, but she runs into push-back from Mellor and the football team. Meanwhile, CB and Glascott are at odds on how to help students resolve their problems, so they create a special kind of club.

After initially trying to sabotage him, CB works with Barry and the JTP to help him win back Lainey’s heart. Meanwhile, Glascott faces removal as principal after a prank damages William Penn Academy.

Lainey is excited to be back to work, but Mellor warns her that being a pal to her students is not a good idea; Principal Glascott introduces the newest science teacher to the faculty, but CB is skeptical of her no-nonsense approach.

Lainey has high hopes for Coach Mellor's love life. Principal Glascott isn't sure how to handle difficult librarian Dr. Ness.

CB chaperones an overnight ski trip and hopes to get in some quality time with Lainey.

Coach Mellor is excited to celebrate Halloween in a couple's costume with Julie, but his plan might be derailed by Principal Glascott. CB tries to scare the students into not tormenting each other during the school's annual Halloween parade.

Lainey is asked to direct another school musical, but she is unsure whether she can top herself after the success of last year's production; Coach Mellor's athletic records may soon be broken, so he must find a way to keep his name in the spotlight.

CB hopes getting Lainey a Beanie Baby for Christmas will show his true feelings for her, but it doesn’t go as planned. Meanwhile, Principal Glascott tries to convince Felicia that she needs to participate and sing a song in a Kwanza play he has written for the students.

The hit film has love on everyone's brain, and Lainey has a realization about CB. Meanwhile, Principal Glascott uses the season's bad football team to teach Coach Mellor how to be both a good winner and a good loser.

In honor of Valentine's Day, Principal Glascott throws a "dating game" based on the show "Singled Out" where Lainey uses the opportunity to figure out her feelings. Meanwhile, Felicia is having body-image issues and Coach Mellor throws a workout camp to help her self-esteem.

While preparing students for the school's show choir, Lainey realizes Wilma might be a better singer than her and gets competitive. Meanwhile, Coach Mellor and Aunt Julie fight over how to parent Toby.

Cool parent Greg distracts CB from being a good teacher to help his son Weasel receive extra credit, while former Principal Ball is upset at Principal Glascott when he approves the use of Ball's parking spot as a community garden.