Additional Voice Talents: John DiMaggio (Dr. Drakken / Motor Ed), Estelle Harris (Mrs. Lipsky), Jason Marsden (Felix Renton), Brian Posehn (Cousin Larry), Raven (Monique), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Tara Strong (Tara), Nicole Sullivan (Shego)
Written By: Brian Swenlin
Directed By: Steve Loter
Ep: 53
Emotion Sickness
Additional Voice Talents: Enrico Colantoni (Dr. Cyrus Bortel), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Raven (Monique), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Brian Swenlin
Directed By: Steve Loter
Ep: 54
Bonding
Additional Voice Talents: Jeff Bennett (), Gary Cole (Dr. Possible), Grey Delisle (), Elliot Gould (), Jennifer Hale (), Andrea Martin (Mrs. Stoppable), Patton Oswalt (Professor Dementor), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Rider Strong (Brick Flagg), Patrick Warburton (Mr. Steve Barkin), Frank Welker ()
Written By: John Behnke & Rob Humphrey
Directed By: Steve Loter
Ep: 55
Bad Boy
Additional Voice Talents: Grey DeLisle (Bride), John DiMaggio (Dr. Drakken), Phil LaMarr (), Nicole Sullivan (Shego), Tara Strong (Tara / Sean), Patrick Warburton (Mr. Steve Barkin), Fred Willard (Jack Hench)
Written By: Nicole Dubuc
Directed By: Steve Loter
Ep: 56
Showdown at the Crooked D
Additional Voice Talents: Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Brian George (Professor Ramesh), Kevin Michael Richardson (Slim Possible), Tara Strong (Joss), Nicole Sullivan (Shego)
Written By: Mark Palmer
Directed By: David Block
Ep: 57
Dimension Twist
Additional Voice Talents: Jeff Bennett (), Clancy Brown (Commander Kane), Danny Cooksey (), John DiMaggio (Dr. Drakken), Jennifer Hale (), Maurice LaMarche (Cable Guy), Rob Paulsen (Kyle), Kevin Michael Richardson (), Nicole Sullivan (Shego), Jonathan Silverman (), Kath Soucie (), James A. Taylor (), April Winchell (Cooking Show Hostess)
Written By: Tracy Berna
Directed By: Steve Loter
Ep: 58/59/60
So the Drama
Starring: Christy Carlson Romano (Kim Possible), Will Friedle (Ron Stoppable)
Also Starring: Nancy Cartwright (Rufus), Tahj Mowry (Wade), Raven (Monique), Gary Cole (Dr. Possible), Jean Smart (Dr. Possible), Shaun Fleming (Jim & Tim Possible), John DiMaggio (Dr. Drakken), Nicole Sullivan (Shego), Ricky Ullman (Eric)
Additional Voice Talents: Diedrich Bader (Lars), Eddie Deezen (Ned), Clyde Kusatsu (Nakasumi), Maurice LaMarche ("Big Daddy" Brotherson), Phil LaMarr (), Kevin M. Richardson (Sumo Ninja / Dr. Gooberman), Stephen Root (Cowboy Gambler), Kirsten Storms (Bonnie Rockwaller), Rider Strong (Brick Flagg), Tara Strong (Tara), Lauren Tom (Yoshiko), April Winchell (Reporter)
Written By: Bob Schooley & Mark McCorkle
Directed By: Steve Loter
Ep: 61
Overdue / Roachie
Additional Voice Talents: John DiMaggio (Dr. Drakken), Brian George (Duff Killigan), Tom Kane (Lord Monkey Fist), Maurice LaMarche (Professor Acari), Patton Oswalt (Professor Dementor), Stephen Root (Chester Yapsby), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Frank Welker (Roachie), April Winchell (Ms. Hatchett)
Written By: Jim Peterson & Brian Swenlin
Directed By: Steve Loter
Ep: 62
Rappin' Drakken
Additional Voice Talents: John DiMaggio (Dr. Drakken), Tom Kane (Judge), Andrea Martin (Nervous Singer), Rob Paulsen (), Sherri Shepard (M.C. Honey), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Bob Schooley & Mark McCorkle
Directed By: Steve Loter
Ep: 63
Team Impossible
Additional Voice Talents: Eric Close (Crash Cranston), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Gary Dourdan (Dash DaMont), Shaun Fleming (Jim & Tim Possible), Patton Oswalt (Professor Dementor), Adam Rodriguez (Burn Burnam), Jean Smart (Dr. Possible), James A. Taylor (), April Winchell (Bernice)
Written By: Rob Humphrey & John Behnke
Directed By: Steve Loter
Ep: 64
Gorilla Fist
Additional Voice Talents: Kaeko Agena (Yori), Tom Kane (Lord Monkey Fist), Melissa McCarthy (DNAmy), Raven (Monique), George Takei (Sensei), James A. Taylor ()
Written By: Bob Schooley & Mark McCorkle
Directed By: Steve Loter
Ep: 65
And the Mole Rat Will Be CGI
Additional Voice Talents: Clancy Brown (Mr. Merl / Henchman), Nestor Carbonell (Señor Senior, Jr.), Gary Cole (Dr. Possible), Shaun Fleming (Jim & Tim Possible), Joe Mantegna (Jimmy Blamhammer), Danny Masterson (Quinn), Ricardo Montalban (Señor Senior, Sr.), Anneliese van der Pol (Heather), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Raven Symone (Monique), James A. Taylor ()