| Episode | Production | Airdate | Title | Notes |
|---|---|---|---|---|
| 99 | 0501 | October 6, 1988 | Together Again and Again | As Theo begins his freshman year at
New York University, Denise announces
that she is dropping out of Hillman College.
Sondra is revealed to be pregnant. First mention of Cliff's theory that the children keep returning home because "they want the house." |
| 100 | 0502 | October 13, 1988 | The Physical | Cliff prepares for a physical. John Amos as Dr. Bradley Herbert, Jr. |
| 101 | 0505 | October 20, 1988 | Rudy's All-Nighter | Rudy's friend sleeps over. |
| 102 | 0503 | October 27, 1988 | Move It (a.k.a. The Baby Game) | Everyone wants pregnant Sondra and Elvin to find a new house. Elvin's surname, Tibideaux, is revealed. |
| 103 | 0504 | November 3, 1988 | Out of Brooklyn | Denise leaves Brooklyn for a job in Africa (Lisa Bonet's last appearance of Season 5). |
| 104 | 0506A | November 10, 1988 | The Birth (1) | Sondra goes into labor, and Elvin is a
nervous wreck. Deon Richmond as Kenny. Michelle Thomas as Justine. First appearances of Reno Wilson as Howard, and Elizabeth Narvaez as Kara. Guest appearance by Naomi Campbell. |
| 105 | 0506B | November 10, 1988 | The Birth (2) | Sondra gives birth to twins -- a boy and a girl -- who are named after Nelson Mandela and his then-wife Winnie. Elvin decides to return to medical school. |
| 106 | 0507 | November 17, 1988 | Cyranoise de Bergington | Theo wants to date his friend Howard's ex-girlfriend, but he is stunned upon learning who she wants to date. Troy Winbush as Denny. Reno Wilson as Howard. |
| 107 | 0508 | December 1, 1988 | How Do You Get to Carnegie Hall? | Vanessa, Janet and Kara want to be professional singers; Russell wins a prize in a sweepstakes, which turns out to be a toaster. Pam Potillo as Janet. Elizabeth Narvaez as Kara. Guest appearance by singer Betty Carter. |
| 108 | 0509 | December 8, 1988 | If the Dress Fits, Wear It | Clair secretly goes on a crash diet and exercise program to lose five pounds in a week so she can fit into a dress. Appearance by Debbie Allen; voice-over by Ahmad Rashād (Phylicia Rashād's sister and husband). |
| 109 | 0510 | December 15, 1988 | Is There a Hamster in the House? | Rudy takes care of a friend's hamster for the weekend. |
| 110 | 0512 | January 5, 1989 | Truth or Consequences | Rudy lies to cover for Vanessa, who secretly goes out on a date with her older boyfriend. |
| 111 | 0511 | January 12, 1989 | Cliff Babysits | While the family attends a Michael Jackson concert, Cliff babysits his grandchildren Nelson and Winnie. First mention of Cliff's younger brother James, who died of rheumatic fever as a child (Bill Cosby's actual brother James died of the same illness at the age of six). |
| 112 | 0514 | January 26, 1989 | Mrs. Huxtable Goes to Kindergarten | Clair appears as a panelist on a local Sunday morning talk show entitled "Retrospective". Clair buys a new couch and Cliff tries to keep the old one. Clair's law firm is identified as Greentree, Bradley & Dexter. |
| 113 | 0513 | February 2, 1989 | The Lost Weekend | With the rest of the family gone for the
night, Theo throws a "small" party that gets
out of control. Troy Winbush as Denny.
Reno Wilson as Howard. First appearance
of Alex Ruiz as Lou. Cameo appearance by
Joie Lee. Phylicia Rashād (Clair), Malcolm-Jamal Warner (Theo), Tempestt Bledsoe (Vanessa), and Elizabeth Narvaez (Kara) appear on the episode of A Different World which airs later that evening. |
| 114 | 0517 | February 6, 1989 | No Way, Baby | Cliff tracks down the grandfather of one of his patients: an expectant teenage mother with no other family. Clair deduces that the charming man is illiterate. Guest appearance by Sammy Davis, Jr. |
| 115 | 0516 | February 9, 1989 | Can I Say Something, Please? | Rudy wants to change some of her rules. Voice-over by Ed McMahon (from The Tonight Show Starring Johnny Carson). |
| 116 | 0515 | February 16, 1989 | The Dead End Kids Meet Dr. Lotus | Theo consults a
voodoo shopkeeper for advice on winning
his girlfriend back. Troy Winbush as Denny. Reno Wilson as Howard. Alex Ruiz as Lou. Michelle Thomas as Justine. Guest appearances by Moses Gunn and Harold Perrineau. |
| 117 | 0519 | February 23, 1989 | The Boys of Winter | Cliff's old basketball friend comes to visit. Guest appearance by U.S. Senator (and former NBA basketball player) Bill Bradley. |
| 118 | 0518 | March 9, 1989 | It Comes and It Goes | Sondra bemoans taking care of the twins. |
| 119 | 0520 | March 16, 1989 | Theo's Women | After catching Theo kissing another woman in the lounge of her dormitory, Justine breaks up with him. Desperate to win her back, Theo turns to Cliff for advice. Michelle Thomas as Justine. First appearance of Vanessa A. Williams as Jade. |
| 120 | 0521 | March 30, 1989 | Birthday Blues | Clair's 46th birthday. |
| 121 | 0522 | April 13, 1989 | A Room With No View | Vanessa and Rudy argue and fight. After the sisters do physical damage to the house, Cliff exiles them to the basement. |
| 122 | 0523 | April 27, 1989 | What He Did for Love | Theo's friend Denny finds an expensive watch and gives it to his girlfriend, but it is soon revealed to be stolen merchandise. Troy Winbush as Denny. Alex Ruiz as Lou. Vanessa A. Williams as Jade. |
| 123 | 0524 | May 4, 1989 | Day of the Locusts | Sondra comes down with strep throat, prompting her mother Clair and Elvin's mother Francine to "steal" the babies. |
| 124 | 0525 | May 11, 1989 | 57 Varieties | Theo wants to go to Egypt for an archaeological dig. Reno Wilson as Howard. Alex Ruiz as Lou. Deon Richmond as Kenny. |
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