Story

1988
Jyou born.

1989
Taichi, Yamato, Sora are born.

1990
Koushiro and Mimi born.

1992
Takeru and Hikari born.

1993
Off screen canon includes:
 Natsuko begins sexually abusing Yamato.

1994
According to Episode ??, Hikari nearly dies when hospitalized for her fever.

1996

Digimon Pilot Movie takes place.

1997
Natsuko and Hiroaki divorce.
Off screen canon includes:
Yamato shoots Natsuko to protect himself and his brother. Natsuko is found to have a brain tumor and her behavior returns to normal after it is removed.

1999

Digimon Adventure takes place.
Off screen canon includes:

Yamato and Jyou share intimacy sometime between Episodes ?? and ??. (Fanfiction Link)

2000

Digimon: Our War Game! takes place in March. During Golden Week, the kids relenquish the Crest Power. Miyako witnesses the battle online and Ken and Ryo defeat Milleniummon.
Off screen canon includes:

Koushiro goes to Jyou for advice on being gay. (Fanfiction Link)

2001
1000 Year Seal Drama CD takes place.
Tegami ~Letter~ Drama CD takes place.
Off screen canon includes:
Yamato starts the Teen-Age Wolves and grown his hair out by Winter of '01.
While visiting his grandmother, Kinu, for the summer, he finds his father's bass guitar. (Fanfiction Link)

2002
2 1/2 Year Break Drama CD  reveals that the TV Station is rebuilt and Hiroaki uses bonus to buy Yamato a new bass guitar. Hiroaki reveals he played in a band as a kid, but didn't sing.
Digimon Adventure: Zero Two takes place.

2003
Drama CD (Valentine's Day) takes place.  
Digimon Adventure: Zero Two ends.
Door to Summer Drama CD takes place.
Digimon Movie: Diaboromon Strikes Back! takes place.
Off screen canon includes:
Yamato recieves another cassette tape from Shizuka. (Fanfiction Link) He also takes up smoking.
Shin and Shuu are kicked out of their father's home.

2004
Drama CD takes place. Iori finds a girlfriend.
Off screen canon includes:
 The Digital World is closed off due to BlackWarGreymon's sacrifice. (Fanfiction Link)
Maid Cafe "Myuu Mew" opens.
Yamato breaks up with Sora in December due to attacking her. (Fanfiction Link)
Taichi and Koushiro begin to date, officially. Taichi is kicked out of his house and after a brief stay with the Ishidas attends a university on athletic scholarship. Taichi has a bully named Eiri.
Takeru begins writing "A Million Points of Light". He also begins to delve heavily into Christianity, slowly becoming a zealot.
Jyou starts embracing his Paganism.
Mimi visits Japan to do guest vocals on the Teen-Age Wolves' final CD and a talent agent finds her.

2005
Off screen canon includes:
Yamato dissolves the Teen-Age Wolves in January after their last concert. (Fanfiction Link)
Yamato beats up Jyou's father. As a result, Jyou's arm is broken and Shou refuses to let Yamato visit Jyou.
Koushiro is attacked by Eiri, leaving him with a scar across his neck. Eiri is imprisoned for 20 years.
Mimi has a party in March for all of the Chosen in hopes of bringing them together. (Fanfiction Link) Mimi moves back to Japan permanently and forms her pop idol band, Sorrow Sea, and releases a debut CD.
Takeru has his brother read the first draft of his book. Yamato finds an interest in space.
Ken starts a study hall program to help give back to his school/community.

2006
Off screen canon includes:
Yamato, Hikari, and Ken return to the Dark Ocean. (Fanfiction Link) As a result, Ken pursues a detective career.
Iori breaks up with girlfriend from 2004.

2007
Off screen canon includes:
Takeru gives Yamato an intervention and Yamato begins to straighten out his life by tutoring with Jyou and Koushiro at Cafe Myuu Mew.
Takeru begins dating Hikari.
Mimi drops out of school to persue her solo career.
Jyou and Nana officially meet.

2008
Off screen canon includes:
During High School Graduation, Yamato tells Takeru about the abuse. They stop talking.
Sora takes over her mother's flower shop business.
Daisuke meets the Natsuko-like girl waitressing at Cafe Myuu Mew: Natsumi.

2009
Off screen canon includes:
Teen-Age Wolves Reunion Tour. Yamato and Mimi date as a publicity stunt. (Fanfiction Link)
Gets tattoos with Daisuke to celebrate his marraige to Natsumi. (Yamato gets a ying yang, Daisuke gets a sleeve of Fladramon).
Iori begins dating Layn Webb.

2010
Off screen canon includes:
Taichi plays in World Cup.
Mimi is dropped from her label on her birthday.
Ken and Miyako begin dating, officially.
Jun travels with Shuu.

2011
Off screen canon includes:
Takeru and Hikari are married. Hikari is pregnant with Lucian.
 Jyou is kicked out of his home and goes to live with his brothers. Shinji is diagnosed with cancer and Jyou's mother enters a medical ward on a permenant basis.
Koushiro creates an OS based on data from the Digital World.
Mimi earns her GED.
Miyako gives birth to Michiru.

2012
Off screen canon includes:
Hikari gives birth to Lucian.
Taichi and Koushiro are married. As a result, Taichi's father no longer speaks to him.
Jyou has a one-night stand with Nana.
Mimi pursues acting.
Natsumi gives birth to Daimu, then passes away.

2013
Off screen canon includes:
Yamato graduates college and is accepted by NASA. Due to Sora's pregnancy, he gives up NASA and begins work at a car repair shop.
Sora tells Yamato she is pregnant. They marry. Sora cuts off all their friends.
Hikari gives birth to Kazuki.
Nana gives birth to Aiko. Shinjiro passes away.
Mimi is impregnated by her manager.
Daisuke opens his first noodle cart.

2014
Off screen canon includes:
Sora cuts off family after she finds out about Yamato's abuse from Hiroaki. She gives birth to Hanako.
Natsuko tries a stronger medication for her relapsed cancer.
Shin moves to South America.
Taichi is in the World Cup for a second time.
Koushiro's sight has deteriorated; he obtains glasses.
Miko passes away and the Takaishi's get a new cat named Mr. Tinkles.
Mimi gives birth to Russell.
Jun returns from her travels with Shuu.
Iori marries Layn.

2015
Off screen canon includes:
Taichi and Koushiro, using a surrogate, have twins: Jaciru and Nakayama. They are premies.

2016
Off screen canon includes:
Layn gives birth to Tomoyo.
Ken and Miyako marry.

2017
Off screen canon includes:
After Sora accuses Yamato of abusing Hanako, Yamato breaks a mirror, leaving his right knuckles scarred.
Sora gives birth to Tsukuyomi. She also begins talking to Yutaka, who took over the Teen-Age Wolves after Yamato "left".
Natsuko's treatment stops working.
Takeru and Yamato talk for the first time in years. They meet at the park with Lucian, Kazuki, and Hanako.
Jyou enters residency.
Hikari begins her teaching career.
Miyako gives birth to Osamu.
Ken reaches detective in the police force.

2018
Off screen canon includes:
While taking Tsukuyomi in for a check up, Yamato meets Tomaru.
Shuu and Jun find their own place, leaving Jyou with the apartment to himself.
Taichi wins the World Cup. Taichi's father suffers a heart attack.
Iori enters law school.

2019
Off screen canon includes:
Natsuko is re-hospitalized.

2020
Off screen canon includes:
Jyou becomes a brain surgeon. Nana is murdered, leaving Jyou with custody of Aiko.
Hikari nearly has an affair with Daisuke (Fanfiction Link).

2021
Off screen canon includes:
Yamato and Takeru stop talking because Yamato refuses to visit his mother.
Jyou gets stalked by Tomaru.
Jaciru makes the Junior Soccer Team.
Daisuke opens his first restaraunt.

2022
Off screen canon includes:
Tomaru is killed in self-defense. Jyou begins to focus on being more of a father.
Taichi is horribly injured in the World Cup tournament, leaving him with a permanent limp/use of a cane.
Daisuke opens his second restaraunt.
Iori becomes a Defense Attorney.
Ken meets Natalie Acevedo, his new partner on the force.

2023
Off screen canon includes:
Yamato now owns the Suiichi Auto Garage.
Taichi's father passes away.
Daisuke opens his third and fourth restaraunts.
Miyako gives birth to Tatsuya.

2024
Off screen canon includes:
No Children takes place. (Fanfiction Link)
Chemo no longer works for Natsuko.

2025
Off screen canon includes:
Walking in the Dark takes place. (Fanfiction Link) Yamato attempts suicide after initiating divorce. Everyone learns of Yamato's abuse. He moves in with Jyou and Aiko and begins dating Jyou again. Yamato applies/accepted into JAXA.
Takeru, against Hikari's wishes, takes his children to visit Natsuko. She nearly molests Kazuki, thinking he is Yamato.
Natsuko dies and at the funeral, Yamato breaks Takeru's nose.

2026
Off screen canon includes:
Snuff takes place. (Fanfiction Link) Divorce is finalized. Yamato gains sole custody of his children.
Eiri is released from prison and kidnaps Nakayama. Ken rescues Nakayama / shoots Eiri. Nakayama is left with lung damage.
Takeru begins to accept his brother / learns Yamato once harbored feelings for him.
Hikari nearly leaves Takeru.
Sora and Yutaka begin dating.

2027
Off screen canon includes:
 To the Moon and Back takes place. Sora kidnaps her children after her mother passes away.
Kazuki begins dating Russell. When Takeru finds out, Kazuki attempts suicide.

2028
Off screen canon includes:
Digimon Adventure: V! takes place. The kids end up stranded in the Digital World.