Main articles: September 2009; November 2009

Sometime during this year...Edit

• Atticus Shane's son died in an accident. His wife, the witch Caitlin uses Expression to try and bring him back to life. However she is consumed by Expression and dies as well, about 6 months after her son.

Ma​y 23Edit

• Elena has a fight with her boyfriend Matt and meets Damon Salvatore.
• When her parents are driving her home, they have an accident. Their car falls off Wickery Bridge. Stefan saves Elena.

SummerEdit

• Stefan observes Elena and decides that he "needs" to get to know her. It is possible that Damon is also observing her.

Augus​tEdit

• Katherine compels a man to pick a fight with Mason Lockwood. Mason eventually kills his friend and thus triggers the werewolf curse. ("Kill or Be Killed")
• It's interesting to learn, from Stevie, that even before Mason had triggered his werewolf curse, he was hanging out with a pack, who did not approve of his relationship with the vampire "Kathy" (Katherine). At this time he began asking questions about the Sun and the Moon Curse. ("Crying Wolf")
• He filmed the transformation and chronicled his experience in a diary, beginning August 31. that Caroline and Tyler find this diary later. ("The Sacrifice")

Septem​berEdit

• When school starts, Elena meets Stefan and later Damon, and her life, and that of her friends, is forever changed. She learns that they are both vampires.
• Damon is killing random people and leaving a trail, to put the town on the trail of vampires (Stefan). He compels Caroline and is feeding on her.
• With the help of Zach and some vervain, Stefan captures Damon, and locks him up in the Cellar. Damon manages to get Caroline to release him, kills Zach and turns Vicki into vampire.
• Vicki bites Jeremy and threatens to kill Elena. Stefan stakes her. Elena asks Damon to erase Jeremy's memory of the incident.
• Bonnie does her first accidental magic.
• September 15 was Mason's first transformation.

November Edit

• Elena and Stefan come to a truce with Damon, Bonnie starts using her magic, Caroline and Matt hook up, Jeremy meets Anna. Alaric Saltzman is the new history teacher/vampire hunter.
• Damon infiltrates the Founder's Council and befriends Sheriff Liz Forbes. He kills Lexi, Stefan's friend, to gain her trust.
• Emily possesses Bonnie and destroys the crystal that would open the tomb. In a fit of rage, Damon almost kills Bonnie. Stefan saves her, giving her his blood.
• We learn Damon's "evil masterplan" to open the Tomb under Fell's Church and release Katherine. Stefan proposes to help him, as long as the other vampires stay locked. Bonnie and her grandmother, Sheila agree to help, as long as all vampires inside the tomb are burned.
• Katherine is not inside the tomb.
• Anna is also working to open the tomb and release her mother.
• Stefan discovers that Elena is adopted, and that her real parents are Isobel Flemming and John Gilbert.
• Sheila dies as consequence of the spell, and all tomb vampires are released.