The following table highlights key episodes from the season's original run:

: Will faces career instability when he loses his primary wealthy client, Harlin Polk. Professionally, he briefly attempts a partnership with Grace that strains their relationship. Personally, he confronts his father, who had been hiding Will's sexuality from colleagues.

: Karen’s life is marked by the heart attack of her unseen husband, Stan. Her relationship with Rosario continues to be a highlight, defined by a mix of genuine affection and constant bickering. Notable Episodes

The second season of the American sitcom Will & Grace consists of 24 episodes that originally aired on NBC from September 21, 1999, to May 23, 2000. Often regarded by critics as one of the series' strongest years, this season balances the introduction of key narrative arcs with the solidified chemistry of the core ensemble.