Timeline

Year	Events	Corresponding Chapter	Source	Notes
More than 100,000 years ago	The age of the gods of ancient times.		According to legend, in chapter 17.
20,000 - 10,000 years ago	The first generation Dragon God is born, tears down the barriers between worlds, and destroys multiple worlds. All races flee to the Human World. The five Dragon Generals betray the Dragon God, and their battle ends in mutual defeat. The Dragon God sends his son Orsted into the future to defeat Hitogami. Demon Dragon King Laplace (one of the five Dragon Generals) is given a mission by the Dragon God. The Dragon God is killed by Hitogami. Laplace escapes the collapsing Dragon World, and begins to wander the Human World as the second generation Dragon God.		First two paragraphs are according to legend. Third and fourth paragraphs are Orsted from chapter 157.	The legend states that all worlds but the Human World were destroyed, but at least the Void World still exists.
10,000 - 8,000 years ago	The age of chaos. The different races in the Human World are mixed together and struggle. Eventually, each race starts to live in different parts of the world. Only the humans and demons continue to quarrel. Laplace begins studying techniques and spells for the sake of defeating Hitogami, with the goal of one day teaching them to Orsted.		First paragraph is according to legend. Second is Orsted from chapter 157.
7,000 years ago	Start of the First Great Human-Demon War.		According to legend.
6,000 years ago	The First Great Human-Demon War is ended when the hero Arusu leads his six comrades to defeat the five Demon Lords and Demon World Emperor Kishirika.		According to legend.
5,500 years ago	Humans wage war on other races and each other for a period of about 500 years.		According to legend.
5,000 years ago	Kishirika revives. Start of the Second Great Human-Demon War, led by Kishirika. The demons ally with the beast race and sea race, and corner the humans.		According to legend.
4,200 years ago	Golden Knight Aldebaran, the Fighting God, appears and turns the tide of the war. At the very end, his attack punches a huge hole in the Great Continent, forming a sea and splitting it into the Central Continent and Demon Continent. The Fighting God was a disciple of Hitogami. His final battle was against Laplace, and caused Laplace's soul to split exactly in half, causing him to lose his memories and be split into two individuals, the Technique God Laplace who seeks to defeat a god and the Demon God Laplace who hates humans. At the same time, the Fighting God armor was broken and fell to the bottom of the ocean. The Second Great Human-Demon War ends.		First paragraph is according to legend. Second is from Orsted in chapter 157. Kishirika also mentioned the battle in volume 4.	Popular legend falsely claims that Aldebaran fought Kishirika, not Laplace. Based on Rudolph's testimony in chapter 210, the identity of the Fighting God in the last battle may have been Badigadi. It's not certain that the Aldebaran of legend and the Fighting God refer to the same person, either (Rudeus just assumed so).
4,200 - 1,000 years ago	A time of peace. Humans gradually segregate demons onto the Demon Continent and blockade it. The demons struggle for resources, and their population drops.		According to legend.
1,000 years ago	Demon God Laplace is born. He unites the demons and subjugates the Demon Continent.		According to legend.
500 years ago	Start of the Laplace War. Laplace persuades the sea race and beast race, and attacks the Central Continent. Quickly gains control of the north and south part, and invades the west from both directions.		According to legend.
About 400 years ago (K0)	The Seven Heroes persuade the sea race to lift the blockade of the sea, and ally with the beast race by holding hostage the children of their heads of families. The last remaining human country, the Asura Kingdom, put all their efforts into a final assault. The Seven Heroes led the Miris holy order of knights and the beast race in an attack on Laplace's stronghold. In the final battle, four of the Seven Heroes die, leaving Dragon God Ulpen, the first generation North God Karuman, and Armored Dragon King Pergius. But Laplace's close allies are annihilated and Laplace is sealed. Ruijerd Supardia also aids the Heroes during the final battle. The war ends.		According to legend. Ruijerd's role was mentioned by himself and Pergius.	The end of the war marked the start of the Armored Dragon Calendar (甲龍歴). Years are K[year] as the author wrote here, the K for Kou (Armored).
Winter of K330	Start of Orsted's time loop. He appears in a nameless forest in the northern part of the Central Continent.		Orsted, chapter 187.
Fall of K373	Roxy Migurdia is born.		Source
Fall of K388	Paul Greyat is born.		Source
Spring of K390	Zenith Greyrat is born.		Source
~K405	Eris Boreas Greyrat is born.
K407	Rudeus Greyrat is born. Sylphiette is born in the fall. The Holy Beast is born. Rinia Dedorudia and Pursena Adorudia are born.	Volume 1 (Holy Beast mentioned in volume 19, Rinia and Pursena turn 15 in volume 8)	Source for Sylphy
K408	Rudeus learns the written language. He begins to read books.	Volume 1
K409	Relying on a magic textbook, Rudeus begins to use magic. He notices that his total amount of mana is being increased. He learns chantless magic.	Volume 1
K410	Rudeus meets Roxy and begins to get taught magic by her. He also begins to get taught swordsmanship by Paul.	Volume 1
K412	Rudeus is led out of the house by Roxy. He becomes a Water Saint-class magician. Roxy goes off on her own. He meets Sylph. A red orb appears in mid-air inside the Boreas estate.	Volume 1 (orb mentioned in volume 2)
K413	Rudeus notices Sylph is a girl (starts to call her Sylphy). Zenith and Lilia become pregnant. Rudeus becomes respected by Lilia. Aisha and Norn are born.	Volume 1
K414	Rudeus is forcibly sent to the house of Boreas Greyrat in the Fittoa region. He meets Ghyslaine and Eris.	Volume 1-2
K415	Rudeus notices the red orb floating in mid-air on the top floor of the Boreas estate.	Volume 2
K417	Rudeus is given Aqua Heartia as a present on his 10th birthday. That night, he and Eris promise he'll be her first 5 years later. The next day, he teleports to the Demon Continent due to the Fittoa region teleport incident. Nanahoshi is summoned. Roxy heads to the Demon Continent in search of Rudeus, and joins up with Elinalise and Talhand. Rudeus receives his first advice from Hitogami. He meets Ruijerd Supardia and begins efforts to redeem the Supard tribe. He founds the adventurer party Dead End. Sylphy becomes Princess Ariel's guard.	Volume 2-3
K418	Rudeus accepts an eye of foresight from Demon Emperor Kishirika Kishirisu. He saves captured beast race children and the Holy Beast. He meets Gisu. He passes the Great Forest's rainy season in the beast race village. He reunites and reconciles with Paul in the Holy Country Milis. Princess Ariel is driven out of the kingdom of Asura.	Volume 4-5
K419	Rudeus reunites with Aisha and Lilia in the kingdom of Shirone. He is confined by Pax and saved by Zanoba. He is almost killed by the Dragon God Orsted at the Red Dragon Mountains. Sylphy enrolls in Ronoa Magic University along with Ariel and Luke.	Volume 6
K420	Rudeus returns to Fittoa, and has his first time with Eris. She parts ways with him the next morning. Eris begins to train at the Holy Land of the Sword.	Volume 6
K422	Rudeus becomes famous as "Quagmire" in the northern part of the central continent. He joins up with Elinalise Dragonroad. He receives an invitation to become a special student from Ranoa Magic University Vice Principal Jinas, and heads toward the university after waiting for the snow to thaw. He enrolls in Ranoa Magic University. He has a chance meeting with Silent Fitts. He meets Rinia Dedorudia, Pursena Adorudia, and Cliff Grimoire. He reunites with Zanoba. Over the course of the year, Zanoba buys Julie, Elinalise and Cliff become lovers, Demon Lord Badigadi invades, and Rudeus meets Nanahoshi again and becomes friends with everyone.	Volume 7-8
K423	Rudeus discovers Fitts's identity. He and Slyphy become lovers. He buys and prepares a house, and marries Slyphy. Aisha and Norn settle into Sharia. Aisha becomes his maid. Norn enrolls in Ranoa Magic University and moves into the dorm. He ignores Hitogami's advice and goes to the continent of Begaritto with Elinalise. Paul dies and Zenith is rescued. He reunites with Roxy. He marries Roxy and Lucy is born.	Volume 9-14
K424	Rudeus becomes a Water King-class magician. Elinalise and Cliff marry.	Volume 14
K425	Formation of the "Norn Greyrat Public Fan Club". Rinia and Pursena graduate. Rudeus becomes a fourth year student. Nanahoshi summons a watermelon from Earth. Rudeus goes to the Sky Fortress to ask Armored Dragon King Perugius about treating Zenith. He goes to the Demon Continent to ask Kishirika about how to treat Nanahoshi's Drine disease. He fights the immortal Demon Lord Atofe. He learns of Hitogami's plans after meeting future Rudeus, and disposes of the mouse with magic stone disease. He is coerced into battling Orsted by Hitogami and with the help of Zanoba and Cliff creates the magic armor. He reunites with Eris. Orsted defeats him and he becomes Orsted's subordinate. He marries Eris. He summons the Holy Beast from the Great Forest, and named him Leo. Orsted orders him to guard Princess Ariel, who ascends to the throne of Asura. He begins training to protect himself and his family.	Volume 14-18
K427	Rinia and Pursena return to Sharia. Zanoba briefly returns to Shirone with Rudeus and company, and becomes Orsted's subordinate. Lara Greyrat is born. Ars Greyrat is born.	Volume 19-20
K428	Cliff and Zanoba graduate. Rudeus begins to gather allies to prepare for Laplace's reincarnation.	Intermission Volume
K429	Rudeus graduates. Cliff returns to Milishion with Rudeus and company. Sieghardt Saladin Greyrat is born.	Intermission Volume, Volume 22-

Orsted's Knowledge of the Future

Year	Event	Possible this loop?
About 30 years later (~K457)	Pax succeeds in a coup d'état, abolishes the monarchy and founds the Shirone Republic.	No (the republic can't be founded without Pax alive)
About 80 years later (~K507)	Laplace is revived. The exact year seems to not be fixed. If the Shirone Republic exists, he's the son of a descendent of one of Pax's subordinates.	Yes.
About 100 years later (~K527)	Final battle against Laplace. End of Orsted's time loop (shortly after the final battle with Laplace).	Yes.