| Season | Episode | Airdate | Episode Title | Story Line |
| 05.01 | 93 | 09/26/2002 | ...And the Horse He Rode In On | A dashing doctor on horseback rescues Grace; Karen debates cheating on her imprisoned husband with hot-blooded suitor Lionel. |
| 05.02 | 94 | 10/03/2002 | Bacon and Eggs | Jack stalks Kevin Bacon, who unwittingly hires him as his personal assistant, and then orders him to find his persistent pursuer. Grace gets a visit from a handsome doctor. |
| 05.03 | 95 | 10/10/2002 | The Kid Stays Out of the Picture | A feud ensues between Will and Grace, whose second thoughts about having his baby are triggered by an infatuation with Leo. |
| 05.04 | 96 | 10/17/2002 | Humongous Growth | A plot hatched by Karen and Jack to reunite the estranged Will and Grace unfolds amid pandemonium at a child's birthday party. |
| 05.05 | 97 | 10/31/2002 | It's the Gay Pumpkin, Charlie Brown | A bicycling adventure tests Will and Grace while up in the Catskills with Leo and his pal in a quest for Halloween pumpkins. |
| 05.06 | 98 | 11/07/2002 | Boardroom and a Parked Place | Mr. Stein, the long-absent senior partner of Will's firm, who shows up unexpectedly to reassume command. Meanwhile, Grace and Jack are shocked to discover that Karen is now living in her limo. |
| 05.07 | 99 | 11/14/2002 | The Needle and the Omelet's Done | Grace accompanies Leo to dinner with his parents. Meanwhile, Jack continues acting classes with Zandra; Will and Karen get Botox injections. |
| 05.08 | 100 | 11/21/2002 | Marry Me a Little | After Grace impulsively accepts a marriage proposal from Leo, there seem to be a million roadblocks between her and an actual wedding (Part 1). |
| 05.09 | 101 | 11/21/2002 | Marry Me a Little More | After Grace impulsively accepts a marriage proposal from Leo, there seem to be a million roadblocks between her and an actual wedding (Part 2). |
| 05.10 | 102 | 12/05/2002 | The Honeymoon's Over | Neat-freak Will's new roomie is sloppy Karen, who moves in and makes herself cozy while Grace honeymoons; Meanwhile, Jack poses incognito out of fear that the "Gay Mafia" has it out for him. |
| 05.11 | 103 | 12/12/2002 | All About Christmas Eve | Christmas Eve merriment turns sour for Will, riled by Grace's capricious requests that keep him from partying with Jack and Karen. |
| 05.12 | 104 | 01/09/2003 | Field of Queens | When Jack convinces Will to join him on a gay soccer team, Will's inept play leaves him warming the bench. Meanwhile, Grace is delighted that Karen is giddy in anticipation of her date with a handsome restaurant owner. |
| 05.13 | 105 | 01/16/2003 | Fagmalion Part One: Gay It Forward | Will and Jack help Karen's cousin who recently decided to come out of the closet at age 35. Grace is puzzled over what to make of her strange bohemian neighbor when she moves into Leo's Brooklyn digs. |
| 05.14 | 106 | 01/30/2003 | Fagmalion Part Two: Attack of the Clones | Will and Jack continue their campaign to adapt Karen's awkward cousin Barry to his new lifestyle. Meanwhile, Grace feels abandoned by Leo when he leaves to offer his medical services to the needy in Africa. |
| 05.15 | 107 | 02/06/2003 | Homojo | Karen is livid when Stan's new girlfriend befriends Jack. Meanwhile, Will and Grace try to re-connect their lagging friendship with a competitive night of board games with their friends. |
| 05.16 | 108 | 02/13/2003 | Women and Children First | Grace has a girl's night in Brooklyn with Karen, Rosario, Ellen and new neighbor Julie. Meanwhile, Jack reconnects with his childhood babysitter and falls back into childhood patterns, befuddling Will. |
| 05.17 | 109 | 02/20/2003 | Fagmalion Part Three: Bye Bye Beardy | A made-over Barry makes a big splash at a chic fund-raiser, where he also unwittingly arouses Will's romantic interest. Meanwhile, Karen duels with her flamboyant rival Beverley Leslie in a war of wills during a silent auction for charity. |
| 05.18 | 110 | 03/13/2003 | Fagmalion Part Four: The Guy Who Loved Me | The pursuit of Barry pits Jack vs Will; lust for a hotel maintenance man consumes Karen, who poses as a maid to lure her prey. |
| 05.19 | 111 | 04/03/2003 | Sex, Losers and Videotape | Will forms a gin-soaked anti-romance club with other lovelorn losers -- his cuckoo boss, Mr. Stein, and Karen. Desperate to learn the tricks of being seductive, Grace enrolls in Jack's acting class. |
| 05.20 | 112 | 04/17/2003 | Leo Unwrapped | Will attempts to surprise Grace for her birthday by sneaking Leo back from Africa. |
| 05.21 | 113 | 04/24/2003 | Dolls and Dolls | Karen searches for a roommate and finds a high-maintenance individual who shares many of her eccentricities; Grace and Jack must intervene when Will uses painkillers as a crutch. |
| 05.22 | 114 | 05/01/2003 | May Divorce Be With You | Karen hires a seemingly immature attorney to argue against Will in her divorce. Meanwhile, a wealthy client comes between Grace and Jack's friendship. |
| 05.23 | 115 | 05/08/2003 | 23 | Stan's sudden death roils Karen, who confronts his mistress at his funeral, and demands that the will be read then and there. |
| 05.24 | 116 | 05/15/2003 | 24 | Karen and the gang sets sail on her yacht to scatter Stanley's ashes in the Caribbean. |