This season premiered on October 27, 1988, after a long period of reruns, indirectly led by the 1988 Writers Guild of America strike.

[1] At the time of the premiere, Night Court moved to Wednesdays, prompting the new series Dear John to fill in that spot.

To compensate that, Woody eavesdrops at Gary's (Joel Polis) bar, but ends up tied and hanged upside-down outside Cheers.

Cliff trains a new postal worker, Margaret O'Keefe (Annie Golden), and they begin a forbidden relationship at a motel.

Ultimately, Cliff decides to stay when the gang sing "The Ballad of the Green Berets", reminding him that he has friends in Boston and pride in his uniform.

Rebecca organizes a party for her boss Mr. Gaines's (Richard Doyle) daughter, Kelly (Jackie Swanson), enlisting Woody and Sam to serve guests.

At closing time, while Sam is expecting Rebecca, Susan enters the bar appearing too excited to wait and kisses him in the office.

Shocked, Sam helps Rebecca carry Susan's body into the bar, where the gang surprise him by appearing behind the counter.

Marriage specialist Dr. Lawrence Crandall (John McMartin) arrives in Boston for a book tour and a drink with Frasier.

Dr. Crandall admits that he planned to seduce Maria and fears that his career and fifteen-year marriage with Valerie (Joanna Barnes) would be over if exposed.

The Crandalls plan to have dinner together, but Lawrence accidentally puts on Maria's blue coat, so Valerie senses someone inside the closet.

[57] The Pittsburgh Post-Gazette described the character of Rebecca Howe as "annoying", and expressed pleasure at rumors that Joan Severance (originally set to play Susan Howe, a role eventually portrayed by Marcia Cross) could replace Kirstie Alley, contending that Shelley Long's departure in the fifth season was still affecting the series.

[55] Conversely, Herb Caen of the San Francisco Chronicle praised this season, including the cast ensemble and their performances, but still missed departed characters Coach and Diane.