This is the timeline of Rule of Rose.
- The world's largest airship is completed. A trip, planned to occur in two months, will go from Cardington, England to India.
- Gregory M. Wilson writes in his diary about his ill son, Joshua.
- Jennifer's parents die in an airship crash which did not even make it that far from its departure. It is mentioned in the "Once Upon a Time" chapter that Jennifer is the sole survivor. She is eventually found by Gregory.
- Due to the airship crash, a lot of children are orphaned, many of which may have gone to Rose Garden Orphanage. There is a theory that many of the children in the game had parents who died in the crash.
- A string of missing children occurs. A notable theory has led to speculation that Gregory has abducted and killed them.
- Wendy and Jennifer decide to go to the Rose Garden Orphanage. On the 28th, Wendy claims she would free Jennifer. It is unclear what they did for the month of February.
- A journal in Hoffman's office can be found, dated March 2: "Recently, the children have been engaging in odd activities and spreading disturbing rumors -- rumors about creatures that come after children who don't clean up and stray dogs that kidnap small tots... It's all very bizarre."
- Sometime this month, Jennifer arrives at the orphanage and is settled in. On her first day at the orphanage, a photo is taken of everyone.
- Jennifer finds a puppy and names him Brown.
- Mr. Hoffman's koi disappears.
- Amanda begins to bear a grudge against Jennifer.
- Martha Carol receives a letter from Anthony Dolittle.
- On November 11, Mr. Hoffman writes in his diary that he will flee the orphanage, leaving Clara and Martha Carol behind.
- On November 23, Martha witnesses Wendy dog-training Gregory.
- On November 24th, Martha writes a letter to Anthony, but it finishes abruptly, leaving speculation that the orphans killed Martha.
- Wendy kills Brown near the end of the month. Jennifer slaps Wendy, and Wendy is demoted. Wendy flees back to Gregory.
- December 20th - Gregory M. Wilson commits the orphanage massacre and Jennifer survives.
It can be assumed that 10 years after the massacre, Jennifer has forgotten about her life at the orphanage and at 19, she relives her childhood in order to remember the oath she made to Wendy and Brown through a dream.