This is a timeline of all known events, shown in chronological order, across all films.
- Grandma Lois, a member of The Midwives Coven, makes a deal with Toby for wealth and fortune; Toby will receive the next baby boy in her family as a result.
- Kristi meets an "imaginary friend" named Toby, who is actually the demon.
- Katie interacts with Toby for the first time when he scratches Dennis's friend, Randy, and she witnesses it.
- Julie and Dennis are killed by Lois and Toby.
- Lois and the Midwives Coven take custody of Katie and Kristi.
- Toby is successfully brought into the real world by the coven after many years of planning in 2013. He (along with the final possessed child, Leila) travel through a supernatural portal back to this point in 1988, where he kills her mother Emily then exits the house, free to roam the real world from this point onwards. (This event isn't present in the timeline until the events of the sixth film unfold, however, as Toby isn't able to enter the real world until all of the events over the subsequent 25 years lead to the completion of his invocation.)
- In the next four years, the coven, specifically one of their leaders named "Kent", teaches Katie and Kristi how to interact with Toby and explains to them how they have special supernatural powers, in addition to training them to use their powers more effectively.
- The sisters realize their ability to see through the eyes of Toby remotely through time. They begin viewing the Fleege family through Toby's eyes, who live in a new house on their property in the year 2013. (Their daughter Leila shares the same birthday as Kristi's yet-to-be-born son Hunter, which makes her the ideal candidate to complete a ritual in the future to bring Toby from his supernatural dimension into the real world.)
- The Rey house burns down, allowing the coven to later build a new house in the future specifically for the purpose of summoning Toby.
- A grown-up Kristi gives birth to Hunter.
- A grown-up Katie meets her boyfriend Micah and they move in together.
- Toby attempts to kidnap Hunter but needs to elicit more fear to gain power before being able to do so.
- Dan, Kristi's husband, makes a deal with Toby for him to haunt Micah and Katie instead, since the possession is able to be transferred to someone else in the same family.
- Micah and Katie realize that a demon is in their house and Katie reveals that she has had past paranormal experiences. Then they contact a paranormal expert who confirms that it is a demon, and recommends a demon expert to them.
- Micah starts to taunt Toby.
- Toby terrorizes Micah & Katie.
- After entering Katie's former house in 2012 in an attempt to save his possessed friend Jesse, Hector is chased through a mysterious "brown door" (a time portal) and ends up in Katie's house in 2006. A possessed Katie walks down the stairs and secretly grabs a knife while Hector pleads Katie for help. She starts screaming as if she was terrified of him. This causes Micah to rush downstairs to see what happened and he starts to beat up Hector before Katie seizes the opportunity and kills Micah.
- Jesse appears possessed and kills Hector. Grandma Lois appears.
- Katie goes to Kristi and Dan's house, kills them, and kidnaps Hunter. (Dan's daughter, Ali, is away on a school trip during the murders and thus survives.)
- Sometime near this point in time, the coven constructs a new house on the Rey property, specifically designed to later lure the Fleege family and to be an ideal portal for their long-term goal of bringing Toby from his dimension into the real world.
- The Nelson family adopts Hunter (who is now named "Wyatt") sometime in the years after his abduction.
- Five years after Hunter's abduction, Katie and Robbie move into the Nelsons' neighborhood.
- Robbie becomes friends with Wyatt.
- Alex begins to notice strange occurrences around her house.
- Katie and Toby kill off the Nelson family, leaving Alex and Wyatt.
- Alex flees to Katie's house, and gets attacked by her inside.
- Alex attempts to flee Katie's house from the backyard, encounters Wyatt and the coven, and Katie kills her off.
- A year later, in California, a teenager named Jesse starts exhibiting signs of possession.
- His friends Hector and Marisol investigate the strange behavior by looking for similar cases and track down Ali, the surviving daughter of Kristi's husband Dan. She has spent the years since her parents' deaths researching The Midwives Coven and their practice of marking pregnant women to possess their children in exchange for wealth or power. It is revealed that they are eventually taken by the coven for a "final ritual" to complete their possession.
- Jesse is abducted by the coven. Hector and Marisol track them to Katie's old house. They attempt to rescue Jesse, but Marisol is killed by the coven members. Hector is chased by a possessed Jesse through a mysterious "brown door" (time portal) that takes them both back in time to the same house in 2006, immediately prior to when Katie kills Micah. (Jesse then kills Hector immediately after Katie kills Micah back in 2006.)
- Kristi impersonates a realtor and sells the relatively new coven-built house (on the old Rey property) to the Fleege family, whose daughter Leila was identified by Kristi and Katie in 1992 as being the ideal host (in conjunction with Kristi's son Hunter) which will allow them to complete their invocation ritual for Toby.
- Leila begins exhibiting signs of possession and starts interacting with Toby. Her father Ryan finds VHS tapes from 1992 of Kent and Lois training Kristi and Katie, and realizes that the sisters were remotely viewing them from the past when they begin reacting on the old 1992 tapes to things that were currently happening in 2013.
- Leila draws runic markings onto her bedroom wall, shown in previous films as being related to Toby and the coven. This supernatural "portal" allows the possessed to travel through time, which gives the coven a way to gather the possessed children from across time and space (similar to the previously used "brown door").
- Leila's parents begin researching her possession and discover that Toby is one of seven "Princes of Hell". They enlist the help of Father Todd, who realizes that Toby is trying to enter the real world by possessing their daughter and using her as the final piece of the coven's ritual.
- They agitate Toby into appearing in his spiritual form then trap him inside of a circle of protection. They use holy water and Bible incantations in an attempt to send him back to his dimension, but he tricks them into thinking he's gone then proceeds to kill Father Todd and Leila's family.
- Leila escapes the house through her bedroom portal while her mother Emily follows her through. They end up in the old Rey house in 1988, and it is revealed that the coven succeeded in its effort to bring Toby into the real world. Toby, in his male humanoid form, kills Emily and leaves with Leila, presumably starting his new life in the real world.