| "Beyond Blunderdome" | [AABF23] | 9/26/99 | Homer lends a hand to Mel Gibson in making a new version of Mr. Smith Goes to Washington. |
| "Brother's Little Helper" | [AABF22] | 10/3/99 | Bart suffers the side effects of a new behavior modifying drug he is given. |
| "Guess Who's Coming to Criticize Dinner" | [AABF21] | 10/24/99 | Ed Asner guest voices as Homer becomes a food critic. |
| "Treehouse of Horror X" | [BABF01] | 10/31/99 | Homer is involved in a Y2K-related problem at the power plant; when Bart and Lisa eat X-rayed candy, they develop superpowers; a takeoff on I Know What You Did Last Summer as the Simpsons try to cover up Ned Flanders' death. |
| "E-I-E-I-D'oh" | [AABF19] | 11/7/99 | The tobacco industry is after Homer and Bart after they develop "Tomacco", a highly addictive tomato-tobacco cross. |
| "Hello Gutter, Hello Fadder" | [BABF02] | 11/14/99 | Penn & Teller and Ron Howard are among the celebrities present after Homer bowls a 300 game. |
| "Eight Misbehavin'" | [BABF03] | 11/21/99 | Apu becomes the father of octuplets, but when he realizes he and Manjula can't raise them on their own, he makes a deal with the Springfield Zoo. |
| "Take My Wife, Sleaze" | [BABF05] | 11/28/99 | John Goodman and Henry Winkler guest star as Homer wins a new motorcycle, only to see Marge kidnapped by a biker gang. |
| "Grift of the Magi" | [BABF07] | 12/19/99 | When Springfield Elementary goes broke, it is sold to a company that turns it into a front for the development of the next "must have toy". |
| "Little Big Mom" | [BABF04] | 1/9/00 | When Marge has to spend some time in the hospital, it's up to Lisa to be the mother of the family. |
| "Faith Off" | [BABF06] | 1/16/00 | Bart thinks he's a faith healer after he manages to remove Homer's head from a bucket at a revival meeting. |
| "The Mansion Family" | [BABF08] | 1/23/00 | When Mr. Burns checks into the Mayo Clinic, Homer watches Burns Manor for him. |
| "Saddlesore Galactica" | [BABF09] | 2/06/00 | Homer and Bart discover the ups and downs of horse racing. |
| "Alone Again, Natura-Diddly" | [BABF10] | 2/13/00 | The Simpsons help Ned Flanders through tough times after losing his wife to an untimely death. |
| "Missionary: Impossible" | [BABF11] | 2/20/00 | Homer joins a missionary. |
| "Pygmoelian" | [BABF12] | 2/27/00 | Moe's new makeover lands him the lead on one of Springfield's hottest daytime soap operas. |
| "Bart to the Future" | [BABF13] | 3/19/00 | Bart finds his future self a ne'er-do-well musician and Ralph Wiggum's room mate. Meanwhile, Lisa seems to be President of the United States. |
| "Days of Wine and D'oh'ses" | [BABF14] | 4/9/00 | Barney quits drinking, leaving Homer feeling resentful; Bart & Lisa enter a contest to photograph the cover of the phone book. |
| "Kill the Alligator and Run" | [BABF16] | 4/30/00 | Kid Rock, Joe C., Robert Evans, and Charlie Rose guest voice as the Simpsons spends Spring Break in Florida. |
| "Last Tap Dance in Springfield" | [BABF15] | 5/7/00 | When Lisa enrolls in a dancing class, she turns out to be better than the teacher, an ex-child star. |
| "It's A Mad, Mad, Mad, Mad Marge" | [BABF18] | 5/14/00 | A woman who is left at the altar by Otto moves in with the Simpsons and out-moms Marge, driving her mad. I am missing trivia for this! Please email me some! |
| "Behind the Laughter" | [BABF18] | 5/21/00 | What if the Simpsons were a real family portraying themselves on TV every Sunday night? What would their lives be when they're not on the air? And how would everybody else in Springfield feel about it? (Season Finale). |