It's 1990-something, and since Lainey still hasn't achieved rock ‘n' roll greatness, she 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.
Lainey and Glascott encounter an overbearing parent and enlist the help of Beverly Goldberg; Mellor realizes he might want to be a father after C.B. shows him how to care for confiscated digital pets.
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 Meanwhile, Glascott and CB struggle to modernize the school's outdated boy's health education program.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 (Hayley Orrantia) and CB. Meanwhile, Mellor's distraught to learn his star athlete alum, Ruben Amaro Jr. (Niko Guardado), sees Glascott as more of a mentor than Mellor
Lainey encourages Glascott to trust his niece and let her get her driver's license, only to find Felicia isn't trustworthy. CB and the student "Star Wars" club bring Mellor along to the premiere of "The Phantom Menace," but Mellor's thoughts on the movie cause the club to dissolve.
As the new cheer coach, Lainey wants to bring the William Penn cheer team to competitions, but she runs into push-back from Mellor and the football team. C.B. and Glascott create a special kind of club.
Lainey and CB encourage a rebellious student radio club until a rogue DJ starts spreading rumors about them. Mellor takes umbrage when Glascott tries to change the school's mascot, so as a result, Mellor tries to get the school on board with a competing mascot.
When CB finally gets the courage to tell Lainey that he has feelings for her, Barry derails his plans; Glascott discovers that he can't make all of the teachers like each other after his plan with the school's staff goes awry.
After initially trying to sabotage him, C.B. 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.
Coach's attempt to help student Toby Murphy feel better like in the movie "Rudy"in an attempt to score with his hot aunt backfires when Toby finds out it was all a lie. Meanwhile, Lainey tries to bond with new teacher Wilma to replace her friendship with Erica Goldberg.
Hoping to improve the football team's chances at winning the title, Coach Mellor and Principal Glascott recruit star soccer player Felicia to kick field goals. But soon, she is treated like one of the guys, which affects her relationship with fellow player Reza. Meanwhile, CB chaperones an overnight ski trip and hopes to get in some quality time with Lainey but is constantly thwarted by socially awkward Tom Scott.
When a bad flu epidemic hits William Penn, Coach Mellor is sent to his sick bed and Principal Glascott must step it up as the wrestling coach with the Jenkintown Cup on the line. Meanwhile, Lainey thinks she can easily pass a class taught by CB, yet it's anything but.
Coach Mellor is excited to celebrate Halloween in a couple's costume with Julie, but his plan might be derailed by Principal Glascott's faculty-parent dating rules. Meanwhile, CB uses "The Blair Witch Project" to attempt to scare the students into not tormenting each other during the school's annual Halloween parade
Coming off the musical success of "Rent" last year, Lainey is asked to direct a school production of "The Lion King," but she fears she can't top herself. Meanwhile, Coach Mellor's athletic records may soon be broken, so he must find a way to keep his name in the spotlight.
CB celebrates Thanksgiving by having all of William Penn rally around him after a cooking incident at his house, while the alumni faculty football game brings out the competitive sides of Wilma and Coach Mellor.
Learning he's not into baseball cards, Coach Mellor encourages Toby to be competitive in CB's Pokemon Club and becomes an overbearing sports-type father. Meanwhile, Lainey supplements her salary as a teacher by working at the local video store and learns an important lesson.
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.
Wilma encourages Ronnie to pursue his dreams of being in a boy band but goes too far when a music video gets out for all of William Penn to see. Meanwhile, the school hires Aunt Julie as the new school nurse which quickly affects her relationship with Coach Mellor.
Principal Glascott and Lainey struggle to agree on what is an appropriate dress code. Coach Mellor struggles with his relationship with Julie because she doesn't enjoy sports like he does.
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.
Wilma steps in to help CB move on from Lainey with help from Coach Mellor, while Lainey learns she has unresolved issues from her past when mentoring a student.
While preparing students for the school's show choir, Lainey realizes Wilma might be a better singer than her and gets competitive; 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.
With some encouragement from Coach Mellor, Lainey reunites with her mother. While inspired by the film "Good Will Hunting," Wilma adds a new, unorthodox addition to the robotics club.
Coach Mellor deals with jealousy issues after learning that Julie is friends with a handsome doctor. Meanwhile, Glascott appoints CB to be substitute principal after his surgery, but needs Lainey to solve a problem with the mean girls of William Penn that he can't.
Smitten with environmental consultant Paloma, who was hired to oversee William Penn's Earth Day activities, CB's feelings may change when he learns she wants to stop an important construction project at the school. Meanwhile, Wilma gets a surprise after convincing Lainey that yearbook superlatives are not important.
Lainey has a difficult choice regarding her relationship with Barry and her friendship with CB. Coach Mellor and Julie are put in a tough parenting position when Toby is invited to prom as a freshman by a senior.
This Goldbergs-inspired special event picks up where the Goldberg family leaves off at William Penn Academy in the 1990s as former teacher and now Head of School John Glascott leads a faculty of teachers with wildly different views on how to mentor students and recruits his tough-as-nails-sister Lucy to join his staff and enroll her teenage daughters Felicia and Gigi as new students. Lucy is desperate to ensure they avoid the social pitfalls of high school and finds herself torn between Glascott's nurturing and communicative approach to parenting and Coach Mellor's tough-guy belief that physical competition brings out the best in students. Even Beverly Goldberg comes to visit the school's staff despite all her kids having already graduated and can't help but meddle one last time.
