Additional Voice Talents: Mindy Cohn (Ms. Whisp), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken / Dr. Zeruda), Shaun Fleming (Jim & Tim Possible), Phil Morris (Lieutenant Franklin / Infinity Guy), Jean Smart (Dr. Possible), Nicole Sullivan (Shego), April Winchell (Tricia Lipowski / Bernice)
Written By: Matthew Negrete
Directed By: Steve Loter
Ep: 23
Grudge Match
Additional Voice Talents: Corey Burton (Robot Rumble Announcer), Gary Cole (Dr. Possible), Shaun Fleming (Jim & Tim Possible), Nika Futterman (Zita), Tom Kenny (Dr. Phen / Lamar), Phil LaMarr (), Rob Paulsen (Theater Boy #1 / Robot Rumble Scanner), Brian Posehn (Cousin Larry), Stacy Sibley (), Shawnee Smith (Vivian), Raven (Monique)
Written By: Gary Sperling
Directed By: Dave Block
Ep: 24
Two to Tutor
Additional Voice Talents: Corey Burton (), Nestor Carbonell (Señor Senior, Jr.), Ricardo Montalban (Señor Senior, Sr.), Rob Paulsen (Francois), Stephen Root (Texan), Kirsten Storms (Bonnie Rockwaller), Raven (Monique), Patrick Warburton (Mr. Steve Barkin), April Winchell (Granny Crocket / Lunchlady)
Written By: Kurt Weldon
Directed By: David Block
Ep: 25
The Ron Factor
Additional Voice Talents: Diedrich Bader (Gamma), Neil Flynn (), Felicity Huffman (Dr. Betty Director), Tom Kenny (Global Justice Scientist / Delta), Maurice LaMarche (Gemini), Raven (Monique), Kevin Michael Richardson (), Frank Welker (Tau)
Written By: Gary Sperling
Directed By: Steve Loter
Ep: 26
Car Trouble
Additional Voice Talents: Jeff Bennett (Toaster / Blender / Ghost Car Narrator), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Susie Essman (S.A.D.I.), Reggie Hayes (Dr. Freeman / Microwave Oven), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Bill Motz & Bob Roth
Directed By: Steve Loter
Ep: 27
Rufus in Show / Adventures in Rufus-Sitting
Additional Voice Talents: Tom Kane (Lord Monkey Fist), Brian George (Duff Killigan), Elliott Gould (Mr. Stoppable), Andrea Martin (Mrs. Stoppable), Phil Morris (Falsetto Jones), Rob Paulsen (Francois / Announcer), Nicole Sullivan (Shego / Computer), Frank Welker ()
Written By: Eddie Guzelian
Directed By: David Block
Ep: 28
Job Unfair
Additional Voice Talents: John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Tom Kenny (Joe / Salesman / Ludwig / Career Week Guy), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Nicole Dubuc
Directed By: David Block
Ep: 29
The Golden Years
Additional Voice Talents: Corey Burton (), Gary Cole (Dr. Possible), Grey Delisle (), John DiMaggio (Dr. Drakken / DJ), Shaun Fleming (Jim & Tim Possible), Debbie Reynolds (Nana Possible), Jean Smart (Dr. Possible), Tara Strong (), Nicole Sullivan (Shego)
Written By: Earl Kress
Directed By: David Block
Ep: 30
Virtu-Ron
Additional Voice Talents: Gary Cole (Dr. Possible), Danny Cooksey (Jake), Shaun Fleming (Jim & Tim Possible), Nika Futterman (Zita Flores), Stephen Root (Mr. Nevius), Martin Spanjers (Malcolm Nevius), Tara Strong (Female Gamer), Raven (Monique)
Written By: Mark Palmer
Directed By: Steve Loter
Ep: 31
The Fearless Ferret
Additional Voice Talents: Grey Delisle (), John DiMaggio (Ferret Fan), Shaun Fleming (Jim & Tim Possible), Tom Kenny (Ferret Fan), John C. McGinley (Rudolph Farnsworth / The White Stripe), Jean Smart (Dr. Possible), Adam West (Timothy North / The Fearless Ferret)
Written By: Brian Swenlin
Directed By: Steve Loter
Ep: 32
Exchange
Additional Voice Talents: Keiko Agena (Yori), Dante Basco (Fukushima), Tom Kane (Lord Monkey Fist), Kirsten Storms (Bonnie Rockwaller), Rider Strong (Brick Flagg), Raven (Monique), George Takei (Sensei), Brian Tochi (Hirotaka), Patrick Warburton (Mr. Steve Barkin)
Written By: Thomas Hart
Directed By: Steve Loter
Ep: 33
Rufus Versus Commodore Puddles / Day of the Snowmen
Additional Voice Talents: Gary Cole (Dr. Possible), Grey Delisle (), John DiMaggio (Dr. Drakken), R. Lee Ermey (General Simms), Shaun Fleming (Jim & Tim Possible), John Kassir (), Philip Morris (Soldiers / Jake the Cameraman / Snowy), Jean Smart (Dr. Possible), Nicole Sullivan (Shego), Hallie Todd (Summer Gale)
Written By: Brian Sintay (story 1), Joseph Molinari (story 2)
Directed By: Steve Loter
Ep: 34/35/36
A Sitch in Time
Additional Voice Talents: Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Michael Dorn (Rufus 3000), Michael Clarke Duncan (Future Wade), Harrison Fahn (), Dakota Fanning (Pre-Kindergarten Kim), Shaun Fleming (Jim & Tim Possible), Vivica A. Fox (Future Monique), Brian George (Duff Killigan), Richard Gilliland (McHenry), Elliott Gould (Mr. Stoppable), Tom Kane (Lord Monkey Fist), Andrea Martin (Mrs. Stoppable), Freddie Prinze Jr. (Future Jim & Tim), Raven (Monique), Kelly Ripa (Future Bonnie), Jean Smart (Dr. Possible), Kath Soucie (Teacher / Cheerleader / Mrs. Mahoney), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego)
Written By: Bill Motz & Bob Roth
Directed By: Steve Loter
Ep: 37
A Very Possible Christmas
Additional Voice Talents: Corey Burton (Drak-Force One Computer), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken / Captain Lewis), Stephen Root (Memphis), Jean Smart (Dr. Possible), Shaun Fleming (Jim & Tim Possible), Edd Hall (TV Announcer), Debbie Reynolds (Nanna Possible), Nicole Sullivan (Shego), Lauren Tom (Yoshiko)
Written By: Mark Palmer
Directed By: David Block
Ep: 38
Queen Bebe
Additional Voice Talents: Bill Barretta (), Jeff Bennett (), Gary Cole (Dr. Possible), Grey DeLisle (), Steve Harwell (Himself), Kerri Kenney (Bebes), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), Tara Strong ()
Written By: Greg Weisman
Directed By: David Block
Ep: 39
Hidden Talent
Additional Voice Talents: John DiMaggio (Dr. Drakken), Patton Oswalt (Professor Dementor), Sherri Shepherd (M.C. Honey), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Michael A. Newton
Directed By: David Block
Ep: 40
Return to Camp Wannaweep
Additional Voice Talents: Justin Berfield (Gil), Corey Burton (Dr. Lurkin), Jason Marsden (Shark Kid), Kirsten Storms (Bonnie Rockwaller), Tara Strong (Tara), Patrick Warburton (Mr. Steve Barkin)
Written By: Matt Negrete
Directed By: David Block
Ep: 41
Go Team Go
Additional Voice Talents: Jere Burns (Mego), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Richard Horvitz (Aviarius), Christopher McDonald (Hego), Fred Savage (Wego), Nicole Sullivan (Shego), Frank Welker (Condor)
Written By: Nicole Dubuc
Directed By: David Block
Ep: 42
The Full Monkey
Additional Voice Talents: Bill Barretta (), Jeff Bennett (Professor Acari / Desk Clerk / Announcer), Shaun Fleming (Jim & Tim Possible), Tom Kane (Lord Monkey Fist / Doug), Jean Smart (Dr. Possible), Kirsten Storms (Bonnie Rockwaller), A.J. Trauth (Josh Mankey), Patrick Warburton (Mr. Steve Barkin), Frank Welker (Chippy / Monkey Ninjas)
Additional Voice Talents: Mayim Bialik (Justine Flanner), Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Melissa McCarthy (Amy "DNAmy" Hall), Raven (Monique), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin), Frank Welker (Professor Allenford / Dino-Thing)
Written By: Gary Sperling
Directed By: Dave Block
Ep: 45
Oh Boyz
Additional Voice Talents: Lance Bass (Robby), Earl Boen (Señor Senior, Sr.), Corey Burton (Officer Hobble), Nestor Carbonell (Señor Senior, Jr.), David Cassidy (Roland Pond), Joey Fatone (Nicky Nick), Shaun Fleming (Jim & Tim Possible), Jim Forbes (TV Host), Jason Marsden (Ryan), Rob Paulsen ("Man Overboard" Host / Benny), Raven (Monique), Justin Shenkarow (Dexter), Jean Smart (Dr. Possible), Tara Strong (Tara), Frank Welker (Mutated Octopus)
Story By: Nunzio DeFilippis & Christina Weir
Teleplay By: Sheryl Scarborough & Kayte Kuch
Directed By: Steve Loter
Ep: 46
Sick Day / The Truth Hurts
Additional Voice Talents: Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Brian George (Duff Killigan), Amy Hill (Dr. Wanda Wong), Maurice LaMarche (Scientist #1 / Dr. Harris / Dr. Kramer), Rob Paulsen (Scientist #2 / Hank Perkins / Dr. Cook / Student), Jean Smart (Dr. Possible), Kath Soucie (Spirit Squad Weekly Interviewer), Kirsten Storms (Bonnie Rockwaller), Tara Strong (Penny), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin)
Written By: Matt Negrete & Tom Hart (story 1), Matt Negrete (story 2)
Directed By: David Block
Ep: 47
Mother's Day
Additional Voice Talents: Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Shaun Fleming (Jim & Tim Possible), Estelle Harris (Mrs. Lipsky), Andrea Martin (Mrs. Stoppable), Roz Ryan (Wade's Mom), Jean Smart (Dr. Possible), Nicole Sullivan (Shego), Frank Welker ()
Story By: Nunzio DeFilippis & Christina Weir
Teleplay By: Thomas Hart
Directed By: Steve Loter
Ep: 48
Motor Ed
Additional Voice Talents: Bill Barretta (Motor Ed's "Main Bro"), Gary Cole (Dr. Possible), John DiMaggio (Motor Ed), Shaun Fleming (Jim & Tim Possible), Jason Marsden (Felix Renton), Stacy Sibley (Racer Girl), Maggie Wheeler (Dr. Renton)
Written By: Laura McCreary
Directed By: David Block
Ep: 49
Ron Millionaire
Additional Voice Talents: William Daniels (Robot Pilot), Eddie Deezen (Ned), John DiMaggio (Dr. Drakken), Kevin Michael Richardson (), Jonathan Silverman (Jimmy Ding), Kirsten Storms (Bonnie Rockwaller), Craig Strong (), Nicole Sullivan (Shego)
Written By: Bill Motz & Bob Roth
Directed By: Nick Filippi
Ep: 50
Triple S
Additional Voice Talents: Earl Boen (Señor Senior, Sr.), Bob Burnquist (Himself), Nestor Carbonell (Señor Senior, Jr.), Max Casella (), Dallas Friday (Herself), Jason Marsden (Sportscaster), Ryan Nyquist (Himself), Raven (Monique), Rider Strong (), Tara Strong (), Trevor Vines (Himself), Patrick Warburton (Mr. Steve Barkin)
Written By: Nicole Dubuc
Directed By: Steve Loter
Ep: 51
Rewriting History
Additional Voice Talents: Gary Cole (Dr. Possible), John DiMaggio (Dr. Drakken), Dave Fennoy (Exterminator), Estelle Harris (Mrs. Lipsky), Tom Kenny (), Patton Oswalt (Professor DeMenz), Kirsten Storms (Bonnie Rockwaller), Nicole Sullivan (Shego), Patrick Warburton (Mr. Steve Barkin), John Witherspoon (Wade's Uncle Wayne)