5.01: “Miss the Alligator and Run”

Homey is left behind on a field trip to the zoo and gets locked in. When he begins to suspect that an alligator may have escaped from it’s cage, he worries that he’ll be trapped in with it all night. Meanwhile, Abe realizes he's missing and searches the town for him.

5.02: “Venice the Menace”

After winning Krusty the Klown’s Krusty Kontest, Homey and friends win a trip to Italy! After enjoying the sights, they find out that the prize doesn’t include tickets home and are stranded. They get jobs as waiters in an Italian restaurant to get money for plane tickets. However, they are sidetracked when they stumble across a Globex super villain’s evil plan.

5.03: “The Great Puppet Caper”

During spring cleaning, Homey discovers a puppet that he won on Fat Tony’s game show (4.13) and finds that it’s stuffed with money. The money is obviously fake, but Homey, being the fool he is, thinks it’s real. When the mafia sees their counterfeit money circulating, they are determined to get it back… or else!

5.04: "Pass the Grave-y"

On a car trip, Homey sees a tombstone with Seymore Skinner's name on it and worries that he must have died in Vietnam. However, Skinner is actually still in jail. Jail is no problem for a former soldier and he soon has his cellmates going straight. When Homey discovers that he's still alive, he's determined to find out who would want the town to think he's dead.

5.05: "Desparate for Ideas"

Homey's teacher assigns the class to write about their lives but they can't think of much. Desparate for ideas, they reminise about their pasts (yes, it's a clip show).

5.06: "The Mart of War"

When Skinner is finally free from jail, he wants to return home, but, on the way, he is shocked to see a store called "War*Mart" selling artifacts from his stay in Vietnam. The objects have sentimental value and he becomes determined to shut the store down.

5.07: “Homey Phobic”

After another failed test at school, Homey stops at Kenny’s Kwik-E-Mart for a hot dog. On the way home, he is chased by a pit bull. The next day, he sees a small dog on the street and runs in terror. It causes him to realize he’s now terrified of dogs. Barney and Kirk now have to break him of his phobia.

5.08: “Return To the ‘C’”

When Homey realizes that his grades seem to be going up, it causes him to wonder if the Simpson gene skips a generation. Sadly, he’s wrong, but his newfound self-confidence allows him to begin excelling in other things.

5.09: “Doctor (Annoyed Grunt)”

Homey becomes suspicious when he hears that a new student named Hank Scorpio may be a supporter of Globex. They suspect it when they hear him complain about the fall of one of it’s greatest plans in Italy (from “Venice the Menace“). The next day, Kirk sees a black Globex van behind Hank’s house and decides to investigate, little knowing that the contents of the van could bring Springfield it’s greatest caper EVER!

5.10: "Mow Better Blues"

Homey accidentaly breaks his skateboard while attempting a stunt and needs money to buy a new one. He starts a lawnmowing business but gets worried when Moe starts a rival mowing service.

5.11: "The Lazy and the Tramp"

Abe gets caught speeding and is sentenced to community service. As his service, he has to let a bum stay in his basement. Homey is angry at first but soon becomes friends with him and is sad when he has to leave.

5.12: "The Ex Files"

It's been two years since Homey's mother disappeared and Abe feels that he's ready to start dating again. He later runs into his old girlfriend who is still unmarried and the two of them start going out. However, Homey doesn't like the idea of someone else taking his mother's place.

5.13: "Little Strummer Boy"

To take his mind off his father's dating, Homey decides to take up a hobby. He finds his father's old guitar in the basement and tries to teach himself to play it.

5.14: "Sherlock Homey"

When the school equiptment shed gets burned down, the whole school is punished. Homey decides to be a detective and try to find out who did it but is shocked when he discovers it may have been Moe.

5.15: "Less Than Chirro"

Krusty is tired of people complaining about confusion from too many things on the menu at Krustyburger and decides to concentrate soley on their famous breakfast chirros. However, things go bad when a rival chirro operation moves to Springfield.

5.16: "Diary of a Mad Lousewife"

Homey finds his mother's old diary in the attic that may explain her disappearence. He begins to read and learns the story of her life. However, he is heartbroken to discover that the final pages are missing and he is no closer to learning about her than he was before.

5.17: "Don't Tell Mom the Babysitter's Ned"

Abe is called out of town on a business trip and Homey gets angry when he discovers that Flanders will be babysitting him.

5.18: "Last Exit to Book Land"

A Simpsons Tall Tales/Bible Stories/Tales from the Public domain- type deal where the teacher loses her lesson plan and, instead, reads the class a story of a very Homey-like Gen. George Washington.

5.19: "Are You There, God? It's Me, Stinky."

A new fad at Springfield Elementary starts where students are recieveing nicknames for achievements. Homey plans a cool skateboard stunt to get a cool nickname, but, on the way, falls in the mud, earning him the name "Stinky". He becomes determined to rid himself of his new title.

5.20: "Five is Too Many" (Season Finale)

A new boy named Stevie McGreggor (mentioned in "My Mother the Carjacker") moves to Springfield Elementary and becomes friends with Homey. However, when Stevie starts to show him up at things he's good at, he worries that his friends may like Stevie more than him.