5.01: Singing your Heart Out
Maggie finds out that there is a chance to get into a Musical that Principal Skinner has organized and she goes along to the auditions but after setting her heart on a certain part she is horrified it has already been taken by Monica, Even though Monica confesses that she can't really sing well she said she wanted a chance to try something new but a very angry Maggie won't stand for it. On the night of the Musical Maggie plots a plan to get back at her sister and ends up embarrassing her on the stage with (what she thinks) a well thought out Prank.
5.02: The Monica Special
Monica for work experience goes to work in Krusty Burger for a day but after one of the Customers got Food Poisoning from the Secret Sauce, Monica tries to come up with a new meal to keep the Company in Business. Her new Burger is a big Success and makes Krusty Burger the most popular place to eat in Springfield but the other Restaurants have a different idea.
5.03: House of Horror V
Story One: Maggie grows wings in the night and all next day strange things keep happening to her.
Story Two: There's a new boy at Springfield Elementary who has got pshyco powers and ends up commanding the school to do his bidding.
Story Three: After a Hurricane, Springfield is hit by a Tidal Wave, Might this be the end of Springfield?
5.04: Folly of Futures
Story One: Diamond is asked to write what might happen in the future of Springfield so she begins on a story of where she lives in an apartment and both she and Maggie are working up in Canada in a Nature Reserve.
Story Two: Maggie is told of her future when she attends college but is a real troublemaker and ends up getting kicked out and disqualified from her exams.
Story Three: Monica finds out that in the not too distant future that she will have a family crisis which causes her to leave Springfield forever.
5.05: An Orphans Life
The Simpson's sign up to a child help project and take in an Orphan Boy from a Month, Maggie is very jealous of the Orphan and feels that Marge is making to much of a fuss over him and makes his stay unbearable until one week before he has to go back to the Orphanage, He tells Maggie his devastating story of how he became an orphan in the first place.
5.06: Friday's Child
Marge and Homer go out for a meal with Betty and Tim (Diamond's Parents) and after Home turns the conversation round to families, Betty and Tim tell the story of how they met and how Diamond was born.
5.07: Just Follow the Rainbow
After a rumour printed in the Gossipy Springfield High Magazine about how Treasure might be buried in the forest there is a raid, as all the kids make plans of how to steal it. Monica on the other hand feels that the entire thing is a scam and won't take part but persuaded by Maggie they manage to reach the spot first but find nothing but an old coke can.
5.08: My Sitter, My Sibling
Marge and Homer go out to a dance and leave Monica in charge, Maggie hating the idea of being bossed around by her younger sister, hides in the attic and refuses to budge. Meanwhile she is keeping herself locked away, she finds a book of old baby photo's and brings back forgotten memories one of which where she was abducted by a stray vulture at the age of two on a day up to Mt. Springfield with her Kindergarten Group.
5.09: The Amazon Maggie
The Simpson's win mystery plane tickets and go on a holiday without their knowing down to the Amazon. While enjoying the Sights, Maggie wanders off and is cornered by a tribe of angry men who are deciding whether or not to offer her as a sacrifice. Maggie manages to escape in the Middle of the night and is adopted by another tribe and has to be rescued once again by her Family who have to trade something to get her back.
5.10: The Mona Maggie
Maggie is asked to have her portrait painted by a rich artist who has just moved to Springfield but the picture becomes so valuable and Maggie becomes famous and with the money she moves her family into Mr. Burns' Old Home. But with the unveiling of the picture someone has a different idea and makes fakes copies of the painting and the Famous Artist is the main suspect. Maggie and the Artist are considered Scam Artists and Maggie becomes the most hated teen in Springfield. Angry at her Public Humiliation Maggie sets out to find out who scammed her.
5.11: To Hollywood and Beyond
Monica runs away with Toby after both Children got a huge telling off from their parents, they make plans to escape to Hollywood together where they might fulfil their dreams of being child actors but their plan is sabotaged as Maggie catches on to what their planning.
5.12: Boredom School
Marge and Homer wonder if a term at Boarding School might help Maggie get better grades after she fails yet another one of her exams. Maggie on the other hand is greatly against the idea and desperately tries to change her Parents minds by acting extra sweet and good and despite their years of Sibling Rivalry, Monica tries to convince Marge and Homer to go back on the idea.
5.13: How to get on the wrong side of your parents
After accidentally breaking Monica's arm in a Skateboarding Duet Maggie feels her relationship between her and Marge is slowly drifting apart. Now mollycoddling Monica all the time Marge feels how she can forgive Maggie for the damage done, Maggie feels like the Forgotten Simpson once again and is found on the top of Mt. Springfield by Monica, crying. The two girls talk over their troubles and eventually come to an agreement. The episode ends with them walking together into the sunset laughing.
5.14: A Day in the Life of Monica (Season Finale)
We see what a day of Monica's is like, we see the world through her eyes and how she escapes and sorts out the troubles of her day.