This timeline attempts to map out Ryo's past using information from the anime and the games. I've tried to fit events in a somewhat logical manner, but there are continuity problems.

1999 - Taichi and company enter the Digital World.

1999 - After the quest for the "Eighth Child" Taichi and Yamato defeat Vamdemon (Myotismon). Summoned again by Gennai, they return to the Digital World.

1999 - Taichi and company defeat Apocalymon. The gate between worlds is sealed.

December 31, 1999 - Ryo is summoned to the Digital World by Agumon to save Taichi and company from Milleniumon.

2000 - Ken receives a Digivice which is later confiscated by Osamu.

2000 - Ken sneaks the Digivice out of Osamu's desk and uses it to travel to the Digital World where he meets Wormmon.

2000 - Ken and Ryo witness the battle between Omnimon and Diablomon on the internet.

2000 - Ryo and Ken travel to the digital world to defeat Millenniumon. Ken is hit by one of the dark spores.

2000 - Ryo defeats Millenniumon during the D-1 Tournaments and is sucked into a time/dimension warp.

200? - Osamu is hit by a car and killed.

200? - Ken becomes the Digimon Kaizer.

2002 - Wormmon sacrifices himself and the Digimental of Miracles is created. Daisuke uses this to defeat the Kaizer. It is later revealed that Ken has little to no memories of his previous experiences in the Digital World prior to becoming the Kaizer.

2002 - Daisuke and the Chosen Children of the world defeat BelialVamdemon with hopes and dreams and everything nice. Oikawa's death restores the Digital World. The gate between both worlds remains open.

200? - Ryo awakens in the Digital World without his previous memories. After some dimension hopping he learns that Millenniumon was originally suppose to be his partner. The Monodramon who is partnered with Ryo during this current adventure, forces a jogress between the two and as a result a new Digiegg is created.

200? - Ryo Akiyama, the Legendary Tamer of the D-1 Card Tournament disappears.

200? - Ruki partners with Renamon, Jenrya with Terriermon. Takato creates and partners with Guilmon.

October 200? - Ruki, Hirokazu and Kenta find Ryo in the Digital World with his partner Cyberdramon, who later de-digivolves into Monodramon.

200? - Ryo (along with Monodramon) return to the real world with Takato and his crew of Digimon Tamers. After defeating D-Reaper the Digimon are pulled back into the Digital World and the portal between both worlds is sealed. Ryo stays in the real world.

200? - Takato discovers that a new portal has opened in Shinjuku Park.

200? - The Digimon return to the Real World and Ryo is reunited with Cyberdramon.

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