Episode 2 : The Kids Are Alright
Dean pressures Sam into traveling to Cicero, Indiana, so Dean can visit an old flame named Lisa (Cindy Sampson), with whom he had a tryst nine years ago.
Episode 3 : Bad Day At Black Rock
Sam and Dean answer a call on their father's old cell phone, alerting them that someone has broken into their dad's secret storage room in New York. They discover that a cursed rabbit's foot has been stolen and call Bobby (recurring guest star Jim Beaver) for help.
Episode 6 : Red Sky At Morning
Sam and Dean investigate the mysterious demise of drowning victims who were nowhere near water at the time of their death. The brothers learn that each of the victims saw a ghost ship shortly before they died.
Episode 8 : A Very Supernatural Christmas
It's Christmas time and, as Sam and Dean investigate a series of murders where the victims have been pulled up through the chimney, Sam realizes they are dealing with a sort of anti-Santa, a demon with roots in pagan lore.
Episode 11 : Mystery Spot
While Sam and Dean are investigating the disappearance of a man from a tourist location, Dean is shot and killed.
Episode 16 : No Rest for the Wicked
Dean's deal with the crossroads demon is up in 30 hours and Dean, Sam and Bobby (recurring guest star Jim Beaver) search for Lilith, who holds the contract. They discover her location and Sam summons Ruby (recurring guest star Katie Cassidy) for help, despite Dean's protests. Ruby warns them that they aren't yet ready to fight Lilith, but they steal her knife and depart for New Harmony, Indiana. In a battle to the death, Sam, Dean and Bobby take on Lilith and all her demons in a last ditch effort to save Dean's life.