Septem​ber 7

• Elena and her brother Jeremy are now living with their aunt Jenna (Miranda's younger sister).
• First day of school in Mystic Falls High School. Elena meets Stefan Salvatore. ("Pilot")

Septemb​er 8

• There is a party in the woods. Damon bites Vicki Donovan.

September 9

• Vicki spends the day in the Hospital.
• Elena meets Damon at the Salvatore Boarding house.
• There is a big meeting in the square to watch the comet, that was last seen 145 years ago (1864)
• Damon threathens to expose Stefan, and bites Caroline.
• Stefan and Elena kiss for the first time.
• Although unseen until "Bloodlines", Anna arrives in town. She is responsible for turning Logan and Ben. (Children of the Damned ) ("The Night of the Comet")

September 10

• Damon spends the day with Caroline, feeding on her. She misses some classes.
• Stefan tries out and makes into the football team.
• Damon attempts to make peace with Stefan, and says that maybe he too can learn to be a "non-living living person".
• Elena invites Bonnie and Stefan for dinner in her house. Caroline and Damon crash in.
• Damon convinces Elena to drop cheerleading. ("Friday Night Bites")

Septe​mber 11

• Stefan gives Elena the necklace with vervain.
• Its the full moon. Tyler picks up a fight with Jeremy over Vicki. Stefan separates the two.
• Damon tries to compel Elena, but it fails.
• Damon kills Coach Tanner trying to prove to Stefan that he has no more "humanity" in him.
• Damon visits Elena in her bedroom while she is sleeping, and caresses her face ("Friday Night Bites")

September 12

• Damon covers his tracks bringing in a Mountain Lion. It is reported that this was the animal responsible for the recent kills.

September 15

• Mason Lockwood transforms into a werewolf for the first time. He records the transformation and write a journal about it as seen in "The Sacrifice" (There is a glitch in the timeline, because the full moon was on the 11th, but when Tyler and Caroline find Mason's Journal, ("The Sacrifice") he puts the date of his first transformation as September 15th)

September 24

• The Founder's Ball is held. Stefan takes Elena and Damon goes with Caroline.
• Tyler invites Vicki, but keeps her away from the party. Vicki splits with him and looks for Jeremy.
• Jenna meets Logan Fell, who she dated in the past. Although she resists, he eventually convinces her to go out for lunch with her.
• Damon gets a crystal from one of the boxes in the exhibit. He drops it when he is captured by Stefan, but Caroline finds and keeps it.
• Stefan and Zach manage to lock Damon in the cellar.("Family Ties")

September 28

• Stefan is keeping Damon locked in the cellar, without blood. His plan is to dessicate his brother, then lock him in the crypt for around 50 years.
• Stefan makes dinner for Elena, and tells her about himself.
• Jenna goes for dinner with Logan Fell. ("You're Undead to Me")

September 29

• "Sexy Suds Car Wash Fund Raiser". Mystic Falls teenagers reveal how much more beautiful than real world people they are. The proceed will go to the athletic team.
• Even weakened by vervain, Damon manages to call on Caroline to help him and open the cellar door. He kills Zach, but is unable to stop Caroline, because he does not have his ring with him.
• Bonnie notices the crystal, and Caroline gives it to her.
• Bonnie sets water on fire, and finally has to admit that something is up with her. She visits her Grandmother Sheila and asks for help.
• Damon bites Vicki Donovan - again.
• Elena finds a photo of Stefan from 1953, when Joseph Salvatore was killed. She asks Stefan what he is. He tells her that she knows already, that he is a vampire. He tells that he will not hurt her, and asks her not to tell anybody.
• Damon finds Vicki's friends and kills all of them, then set them on fire.
• Logan convinces Jenna to invite him for dinner at her house, and steals the "Gilbert Watch", that is actually a vampire compass. ("You're Undead to Me") ("Lost Girls")

September 30

• Stefan meets Elena at an outdoor cafe to answer her questions about vampires.
• Damon spends the day bored and impatient trapped inside the boarding house. He gave Vicki his blood to heal her, so he could have some company. After she tells him her life story he decides that only death can help her and breaks her neck. She wakes up in transition.
• Logan Fell shoots at Stefan and Vicki with wooden bullets. Damon saves them and kills Logan.
• Vicki feeds on Logan's blood and completes the transition.
• Elena breaks up with Stefan. ("Lost Girls")

There is a time warp! Its the next day in Mystic Falls, but the next episode is during Halloween, October 31st.

October 31 - Halloween

• Vicki is not dealing well with her transition. Stefan wants to convince her to live in animal blood, but she cannot resist the bloodlust.
• She bites Jeremy, and when Elena tries to pull them appart, she bites Elena. Stefan stakes Vicki in front of Jeremy.
• Elena asks Damon to erase Jeremy's memory of what has happened.
• Sheila recognizes that the crystal belonged to Emily Bennett. ("Haunted")