Guest Starring: Samantha Smith (Mary Winchester), Andrea Menard (Sheriff Christine Barker), Carlena Britch (Miriam), Ish Morris (Conrad), Rob Raco (Clark Barker)
Co-Starring: Erika Walter (Lily), Brett Kelly (Pirate Pete Worker), Hyuma Frankowski (Deputy Earl Perkins)
Written By: Andrew Dabb
Directed By: Phil Sgriccia
Ep: 266
The Rising Son
Guest Starring: Samantha Smith (Mary Winchester), Christian Keyes (Alternate Universe Michael), Keith Szarabajka (Professor Donatello Redfield), Jeffrey Vincent Parise (Asmodeus)
Co-Starring: Eric Breker (Alternate Universe Hunter), Ryan S. Williams (Angel Commander), Alex Barima (Drexel), Adil Zaidi (Drunk Demon), Mark Sweatman (Tattooist), Aubrey Arnason (Bartender), Michelle Clarke-Brown (Female Demon)
Written By: Eugenie Ross-Leming & Brad Buckner
Directed By: Thomas J. Wright
Ep: 267
Patience
Special Guest Star: Loretta Devine (Missouri Moseley)
Guest Starring: Kim Rhodes (Sheriff Jody Mills), Clark Backo (Patience Turner), Jon Cor (The Wraith), Adrian Holmes (James Turner)
Co-Starring: Chelsey Reist (Dede), Chanelle Peloso (Ronson), Karen Khunkhun (Newscaster), La'Mya Jackson (Young Patience), Elijah Silva (Convenience Store Clerk)
Written By: Robert Berens
Directed By: Robert Singer
Ep: 268
The Big Empty
Guest Starring: Courtney Ford (Kelly Kline), Rukiya Bernard (Mia Vallens), Niall Matter (Buddy)
Co-Starring: Matt Hamilton (Wes Bailey), Kayla Deorksen (Erica Bailey), Janet Glassford (Bailey's Neighbor), Brenda Matthews (Gloria Simon), Brenden Sunderland (Scotty Simon), Alan Silverman (Roadside Assistant), Brandy Le (Receptionist), John Emmet Tracy (John Driscoll)
Written By: Meredith Glynn
Directed By: John Badham
Ep: 269
Advanced Thanatology
Guest Starring: Seth Isaac Johnson (Shawn Raider), Alisen Down (Penny Raider), Lisa Berry (Billie)
Co-Starring: Kayla Stanton (Jessica), Sacha M. Romalo (Dr. Audrey Meadows), Josh Hudniuk (Evan Meyers), Micah Solis (Mike Ramos), Dan Vaida (Ghost)
Written By: Steve Yockey
Directed By: John F. Showalter
Ep: 270
Tombstone
Guest Starring: Sarah Troyer (Athena Lopez), Jonathan Cherry (Dave Mather), Eric Schweig (Sergeant Joe Phillips)
Co-Starring: Paul C. Grenier (Carl Phillips), Jason Asuncion (Lenny), Hana Kinani (Shawnte)
Written By: Davy Perez
Directed By: Nina Lopez-Corrado
Ep: 271
War of the Worlds
Guest Starring: Osric Chau (Alternate Universe Kevin Tran), David Haydn-Jones (Arthur Ketch), Jeffrey Vincent Parise (Asmodeus), Christian Keyes (Alternate Universe Michael), Farrah Aviva (Daniela), Erica Cerra (Dumah)
Guest Starring: Samantha Smith (Mary Winchester), Kim Rhodes (Sheriff Jody Mills), Clark Backo (Patience Turner), Yadira Guevara-Prip (Kaia Nieves), Adrian Holmes (James Turner), Nathaniel Arcand (Derek Swan), Elfina Luk (Elewon)
Co-Starring: Ella Cannon (Paula Swan), Brahm Taylor (Male Angel), Milo Shandel (Counselor)
Written By: Robert Berens
Directed By: Phil Sgriccia
Ep: 274
Wayward Sisters
Guest Starring: Kim Rhodes (Sheriff Jody Mills), Kathryn Newton (Claire Novak), Briana Buckmaster (Sheriff Donna Hanscum), Katherine Ramdeen (Alex Jones), Clark Backo (Patience Turner), Yadira Guevara-Prip (Kaia Nieves)
Co-Starring: Eden Summer Gilmore (Amanda Fitzmartin), Matthew Afonso (Ed), Shane Leydon (Older Werewolf), Zenaida Telfair (Registered Nurse), Devon Ferguson (), Maria Claire Turner (Mrs. Fitzmartin)
Written By: Robert Berens & Andrew Dabb
Directed By: Phil Sgriccia
Ep: 275
Breakdown
Guest Starring: Briana Buckmaster (Sheriff Donna Hanscum), Brendan Taylor (Office Doug Stover), Chris William Martin (Agent Clegg), Steven Yaffee (Marlon)
Co-Starring: Troy Jay Skog (Pastor "Diamond" Don Hankey), Sarah Dugdale (Wendy Hanscum), Camille Atobo (Felix the Cat), Parker Brando (The Cutter), Jason Vaisvila (Bearded Man), Emilio Merritt (Luis Fernando)
Co-Starring: Shane Dean (Dipper), Sean Tyson (Marty), Mike Kovac (Dale), Angela Moore (Brenda), Adam Klassen (Hardware Store Clerk), Sharon Simms (Mother Plum)
Written By: Steve Yockey
Directed By: Amanda Tapping
Ep: 277
Devil's Bargain
Guest Starring: David Haydn-Jones (Arthur Ketch), Keith Szarabajka (Professor Donatello Redfield), Jeffrey Vincent Parise (Asmodeus), Danneel Ackles (Sister Jo), Erica Cerra (Dumah), Richard Speight, Jr. (Trickster / Gabriel)
Co-Starring: Neil Webb (Tim), Robert Rozen (Cupid), Shane Kim (Demon), Leslee Achorn (Old Woman With Walker), Michael Germant (Scarred Young Man), Robert Gordon Harvey (Groom-to-Be), Forrest Rozitis (Boy #1), Jesse Chongo (Boy #2), Simon Leung (Staring Pedestrian)
Written By: Eugenie Ross-Leming & Brad Buckner
Directed By: Eduardo Sánchez
Ep: 278
Good Intentions
Special Guest Star: Jim Beaver (Alternate Universe Bobby Singer)
Guest Starring: Samantha Smith (Mary Winchester), Keith Szarabajka (Professor Donatello Redfield), Christian Keyes (Alternate Universe Michael), Chad Rook (Zachariah)
Co-Starring: Michael Jonsson (Gog), Andre Tricoteux (Magog), Elinet Louicius (Hunter), Cassidy Nugent (Camp Girl)
Co-Starring: Dino Dinicolo (Antonio Miele), Shaun Omaid (Scarpatti's Thug #1), Tyson Bellusci (Scarpatti's Thug #2), Fei Ren (Diner Woman), Kai Bradbury (Clerk), Demord Dann (Greenstreet's Bodyguard)
Written By: Robert Singer & Andrew Dabb
Directed By: Amanda Tapping
Ep: 280
ScoobyNatural
Co-Starring: Frank Welker (Fred Jones / Scooby Doo), Grey Griffin (Daphne Blake), Matthew Lillard (Shaggy Rogers), Kate Micucci (Velma Dinkley), Dee Bradley Baker (Phantasm), Eric Bauza (Cousin Slicker), Stephen Stanton (Cosgood Creeps), Fred Tatasciore (Colonel Sanders / Phantasm), Peter New (Jay), Michael Girardin (Alan), Kegan Frith (Ghost Kid)
Written By: Jim Krieg & Jeremy Adams
Directed By: Robert Singer
Ep: 281
The Thing
Guest Starring: Richard Speight, Jr. (Gabriel), David Haydn-Jones (Arthur Ketch), Jeffrey Vincent Parise (Asmodeus), Magda Apanowicz (Sandy Porter), Tiffany Smith (Ophelia Avila)
Co-Starring: Enid-Raye Adams (Joanne), Ivan Wanis Ruiz (Marco Avila), Carl Montoya (Diego Avila), Lee Page (Asmodeus' Guard), Sean Depner (Buck), Chiara Guzzo (Amy)
Written By: Davy Perez
Directed By: John F. Showalter
Ep: 282
Bring 'em Back Alive
Guest Starring: Richard Speight, Jr. (Gabriel), David Haydn-Jones (Arthur Ketch), Jeffrey Vincent Parise (Asmodeus), Danneel Ackles (Sister Jo), Erica Cerra (Dumah), Marco Grazzini (Alternate Universe Angel Commander)
Special Guest Star: Felicia Day (Alternate Universe Charlie Bradbury)
Co-Starring: Corey Schmitt (Bounty Hunter), Curtis Tweedie (Young Priest), Tim Beckmann (Father Davis), Bianca Caroca (Possessed Girl), Richard O'Sullivan (Demon)
Co-Starring: Kayla Stanton (Jessica), Jason William Day (Bernard), Sherilyn Allen (Elizabeth Mahler), Blake Stadel (James Melford), Franckie François (Martin), Luc Roderique (Indra)
Written By: Steve Yockey
Directed By: Nina Lopez-Corrado
Ep: 284
Unfinished Business
Guest Starring: Samantha Smith (Mary Winchester), Richard Speight, Jr. (Gabriel), Osric Chau (Alternate Universe Kevin Tran), Tarun Keram (Jakob)
Co-Starring: Sandy Robson (Fenrir Odinsbane), Michael Adamthwaite (Narfi), Fletcher Donovan (Sleipnir), Mark Fraser (Porn Star), Lia Lam (Porn Star), Luke Sykes (Porn Star), Andre Scott (Porn Star), Lindsay Maxwell (Porn Star), Mercedes Gendron (Porn Star)
Written By: Meredith Glynn
Directed By: Richard Speight, Jr.
Ep: 285
Beat the Devil
Guest Starring: Samantha Smith (Mary Winchester), Richard Speight, Jr. (Gabriel), Ruth Connell (Rowena MacLeod), Katherine Evans (Maggie)
Co-Starring: Michael Patric (Floyd), Trevor Lerner (Bartender)
Written By: Robert Berens
Directed By: Philip Sgriccia
Ep: 286
Exodus
Special Guest Star: Jim Beaver (Alternate Universe Bobby Singer)
Guest Starring: Samantha Smith (Mary Winchester), Richard Speight, Jr. (Gabriel), Ruth Connell (Rowena MacLeod), David Haydn-Jones (Arthur Ketch), Christian Keyes (Alternate Universe Michael), Katherine Evans (Maggie), Alexander Cendese (Angel Commander)
And: Felicia Day (Alternate Universe Charlie Bradbury)
Co-Starring: Jeffrey Joseph (Andy), James Lafazanos (Resistance Traitor), Patrick Carlos (Fake Prisoner), Dagan Nish ()
Written By: Eugenie Ross-Leming & Brad Buckner
Directed By: Thomas J. Wright
Ep: 287
Let the Good Times Roll
Special Guest Star: Jim Beaver (Alternate Universe Bobby Singer)
Guest Starring: Samantha Smith (Mary Winchester), Christian Keyes (Alternate Universe Michael), Katherine Evans (Maggie)
Co-Starring: Stephi Chin-Salvo (Ryan), Agape Mngomezulu (Nate), Jag Bal (Werewolf)