Guest Starring: Jim Beaver (Bobby Singer), Sterling K. Brown (Gordon Walker), Jon Van Ness (Creedy), Michael Massee (Kubrick)
Co-Starring: Hrothgar Mathews (Grossman), Christian Tessier (Wayne), Stephen Dimopoulos (Restaurant Owner), Forbes Angus (Foster), John F. Parker ()
Written By: Ben Edlund
Directed By: Robert Singer
Ep: 48
Sin City
Guest Starring: Jim Beaver (Bobby Singer), Martin Papazian (Richie), Sasha Barrese (Casey), Robert Curtis Brown (Father Gil)
Co-Starring: Don S. Davis (Trotter), Gavin Buhr (Bodyguard), Dean Paul Gibson (Bartender), Julia Anderson (Woman at Bar), Richard Keats (Andy Johnson), Gregory Bennett (), Todd Curran (), Matthew Harrison (), Elisa King (Cheryl), Phoebe Greyson ()
Written By: Robert Singer & Jeremy Carver
Directed By: Charles Beeson
Ep: 49
Bedtime Stories
Guest Starring: Christopher Cousins (Dr. Garrison), Sandra McCoy (Crossroad Demon)
Co-Starring: Kimberley Warnat (Julie Watson), Aron Eastwood (Clint), Ava Hughes (Young Callie), Chris Cochrane (), Michael Coleman (Jack Baycon), Malcolm Scott (), Maxine Miller (Old Woman), Patrick Gilmore (Ken Watson), Peter Jenkins (), Libby Osler (), Tracy Spiridakos (Callie), Victoria Duffield (Granddaughter), Mary Black (Grandmother), Derek Lowe (EMT)
Written By: Cathryn Humphris
Directed By: Mike Rohl
Ep: 50
Red Sky at Morning
Guest Starring: Ellen Geer (Gertrude Case)
Co-Starring: Robert Moloney (), Samantha Simmonds (Sheila Case), Michael Denis (), Tobias Slezak (Steve Warren), Steve Lawlor (Water Ghost), Steve Archer (Security Guard), Peter Grier ()
Written By: Laurence Andries
Directed By: Cliff Bole
Ep: 51
Fresh Blood
Guest Starring: Sterling K. Brown (Gordon Walker), Michael Massee (Kubrick), Matthew Humphreys (Dixon)
Co-Starring: Mercedes McNab (Lucy), Damon Johnson (Lucy's Victim), Clare Elliott (Women at Bar), Daniella Evangelista (Hanging Victim), Natalia Minuta (Hanging Victim), Jon Kralt (Driver with Flat Tire), Katie Chapman (Gordon's Victim)
Written By: Sera Gamble
Directed By: Kim Manners
Ep: 52
A Very Supernatural Christmas
Guest Starring: Ridge Canipe (Young Dean), Colin Ford (Young Sam), Spencer Garrett (Edward Carrigan), Merrilyn Gann (Madge Carrigan)
Co-Starring: Emily Holmes (), Zak Ludwig (), Don MacKay (), Alex Bruhanski (), Dryden Dion (), Brandy Heidrick (), Connor Levins (Jimmy Caldwell), Douglas Newell (), Victoria Bidewell (Molly Johnson), Jennifer Copping ()
Co-Starring: Rebecca Robbins (Amanda Burns), Jonathan Watton (Paul Dutton), Ken Tremblett (Ron), Robinne Fanfair (Janet Dutton)
Written By: Ben Edlund
Directed By: Robert Singer
Ep: 54
Dream a Little Dream of Me
Guest Starring: Jim Beaver (Bobby Singer), G. Michael Gray (Jeremy Frost), Cindy Sampson (Lisa Braeden)
Co-Starring: Myriam Sirois (Maya Sanders), Tammy Hui (Maid), Martin Christopher (Doctor), Elizabeth Marleau (Wife), Adrian Formosa (), Damon Runyan (Henry Frost)
Teleplay By: Cathryn Humphris
Story By: Sera Gamble & Cathryn Humphris
Directed By: Steve Boyum
Ep: 55
Mystery Spot
Guest Starring: Jim Beaver (Bobby Singer), Richard Speight, Jr. (Trickster)
Co-Starring: Andrew McIlroy (Mr. Carpiak), Brock Johnson (), Rob deLeeuw (Piano Mover), Lloyd Berry (Mr. Pickett), Dean Moen (), Denalda Williams (Doris), Kasey Kieler (), Derek Green (), David Abbott (Hasselback), Katherine Horsman (Hasselback's Daughter)
Teleplay By: Jeremy Carver
Story By: Jeremy Carver & Emily McLaughlin
Directed By: Kim Manners
Ep: 56
Jus In Bello
Guest Starring: Charles Malik Whitfield (FBI Special Agent Victor Henriksen), Stoney Westmoreland (Deputy Phil Amici), Aimee Garcia (Nancy Fitzgerald), Peter DeLuise (FBI Deputy Director Steven Groves), Tyler McClendon (Sheriff Melvin Dodd)
Co-Starring: Kurt Evans (FBI Agent Calvin Reidy), Rachel Pattee (Lilith), Val Cole (News Anchor), Ron Robinson (Possessed Man)
Co-Starring: John Desantis (Freeman Daggett), Dave Hospes (Shooting Victim), Tony Morelli (Train Victim)
Written By: Ben Edlund
Directed By: Phil Sgriccia
Ep: 58
Long-Distance Call
Guest Starring: Jeffrey Dean Morgan (John Winchester), Tom O'Brien (Clark Adams), Anjul Nigam (Stewie Meyers), Cherilyn Wilson (Lanie Greenfield)
Co-Starring: Eric Breker (Police Officer), Ingrid Torrance (Mrs. Waters), John Shaw (), David Neale (Ben Waters), Anna Mae Routledge (Museum Tour Guide), Dawson Dunbar (Simon Greenfield), Thomas Michael Dobie ()
Written By: Jeremy Carver
Directed By: Robert Singer
Ep: 59
Time is on My Side
Guest Starring: Jim Beaver (Bobby Singer), Steven Williams (Rufus Turner), Billy Drago (Doc Benton), Peter Birkenhead (Mr. Beetle), Adrian Holmes (Demon)
Co-Starring: Kavan Smith (Gym Club Victim), Terence Kelly (Doctor), Marilyn Norry (Nurse), Craig Veroni (), Kaleena Kiff (Female Victim), Nathaniel Marten (Jogger), Tiera Skovbye (Young Bela), Roan Curtis (Lilith)
Written By: Sera Gamble
Directed By: Charles Beeson
Ep: 60
No Rest For the Wicked
Guest Starring: Jim Beaver (Bobby Singer), Sierra McCormick (Fremont Girl), George Coe (Pat Fremont), Jonathan Potts (Mr. Fremont), Anna Galvin (Mrs. Fremont)
Co-Starring: Peter Hanlon (Tom Wepram), Bradley Loree (Police Officer)