Timeline

Below is my thoughts on a possible timeline for the Drenai world. I've included some reasoning as well. The timeline is split into several different sections, this is because it is impossible to acurately put a figure between the different time periods.

The first section is that conserning the Waylander series of books. I am reasonably happy with the placement of events within this period of Drenai history. There is enough supporting evidence about the events to back it all up.

Year
Book
Events
Reasoning
0WaylanderWaylander rescues the prist Dardilion. Along his travels he also rescues Danyal, Kyrlla, Miriel and Culas.Chapter 2 of Waylander tells us that the twin girls are seven years old.
5 Danyal is killed in a riding accident.At the start of Waylander 2, it is said that Danyal died 5 years ago.
7 Princess Aldania, the exciled Drenai Monarche, marries.It is said in HITS that she has been married for 22 years. She got married soon after she was told she was not wanted to rule the Drenai. The 7 years featured here etween the killing of King Nailliad and the marrage is justified by several years passing between the killing and the Drenai finally regaining a stable country.
10Waylander 2Waylander is being hunted by the Guild.Miriel said that she is 17, almost 18! 10 years have passed since the happenings in Waylander.
12 Karnak beats the ventrians and then increases the bounty on Waylander.The epilogue in Waylander 2 covers this.
15 Karnak is killed in a parade celebrating a victory. He is shot with Waylanders crossbow....Covered in epilogue.
23 Waylanders "Skull" is sold.Covered in Epilogue.
29Waylander 3Waylander is getting bored in Kydor, and plans to leave. Just one week too late!Matze Chai informs us that he bought the skull of Waylander 6 years ago.
    

The time between the Waylander series of books and the Druss series is very hard to calculate. I have included the events from the Waylander books in the timeline below with the Legend and onward events. All the events which I am not sure about are highlighted in red, these are my guesses on when things took place, and there is no evidence as to where they actually took place.

-175?Waylander is born in the lands of the Drenai.Waylander's friend in the army, Galen, was 41 at the time of Waylander. As he and Waylander were very good friends, I am assuming that this was because they were of similar age. I could be wrong.
-154?Dakeyras' family are murdered by wandering mercenaries.It is said in Waylander that Waylander's family was killed 20 years ago.
-134?WaylanderWaylander rescues the prist Dardilion. Along his travels he also rescues Danyal, Kyrlla, Miriel and Culas.Chapter 2 of Waylander tells us that the twin girls are seven years old.
-129?Danyal is killed in a riding accident.At the start of Waylander 2, it is said that Danyal died 5 years ago.
-127?Princess Aldania, the exciled Drenai Monarche, marries.It is said in HITS that she has been married for 22 years. She got married soon after she was told she was not wanted to rule the Drenai. The 7 years featured here etween the killing of King Nailliad and the marrage is justified by several years passing between the killing and the Drenai finally regaining a stable country.
-124?Waylander 2Waylander is hunted by the Guild. The Gothir attack the Nadir Wolfshead tribe and lay seige to them at the fortress of Kar-Barzac.
-123?Senta and Miriel's son is born.This would have happened roughly 9 months after the seige of Kar-Barzac.
-122?Karnak beats the Ventrians and then increases the bounty on Waylander.The epilogue in Waylander 2 covers this.
-123?Ekodas and Shia's daughter is born.
-122?Barden is born. [see note 1]When Barden is killed, he is refered to as "The Old Wolf". After much deliberation about this, I have put him as being 55 at his death. A warrior at this age is not out of the question, just look at Druss in Legend! Must be in the Genes!
-119?Karnak is killed in a parade celebrating a victory. He is shot with Waylanders crossbow....Covered in epilogue.
-111?Waylanders "Skull" is sold.Covered in Epilogue.
-105?Waylander 3Waylander is getting bored in Kydor, and plans to leave. Just one week too late!Matze Chai informs us that he bought the skull of Waylander 6 years ago.
-94?Okai's father is born. He becomes a mighty leader of the Wolfshead tribe.
-81 Bress is born.Bress is said to be 21 when Druss is born.
-67 Barden is killed.Bress is said to be 14 when he witnesses his father being killed.
    
-60 Druss is born.He is 60 in Legend...
-49 Okai/Talisman/Ulric is born.He is 49 years old during Legend.
-42Druss the LegendBress is killed by raiders.Druss is 18 when his father is killed.
-36 The final battle of the Ventrian-Naashan Wars.Now the war has ended, Gorben can rebuild his nation. A home is built for the Immortals in Usa....
-15Druss the LegendThe battle at Skeln Pass.Druss is 45 here, which puts the event 15 years before Legend.
0LegendThe First Nadir war. The seige of Dros Delnoch.I have placed the book legend at time 0 because it is the constant that "most" of everything else can be worked out from.
100King Beynd the GateThe Drenai ruler Ceska has gone. The Drenai people are rebelling. Tenaka Khan leads the rebellion and brings the Nadir to the rescue of the Drenai people.The book clearly states on the back cover that it is set 100 years after the events of Legend.
114 Tenaka Khan invades the Drenai Lands.

Taking into account the time the events in KBTG take to run and the fact that Chareos was 12 when he was sent from Dros Delnoch, I believe 14 years passed between the KBTG book and the invasion of the Drenai by the Nadir.

146Quest for Lost HeroesI really complex story about the ghost of Tenaka Khan and the Earl of Bronze.Chareos is 44 when the story begins, therefore I've placed it 32 years after the invasion of the Drenai by the Nadir.
147 The Twins are born.I've added a year here because of the amount of time which passes during the book.
161 The Twin which recides with Chareos stops outside Castle Tenaka....This moment is mentioned as happening 14 years after the birth of the twins.
176?War of the Twins?It is difficult to place this war. It must happen some time after the scene outside Castle Tenaka because it just doesn't seem ready for the situation of war. I've added 15 years to the timeline and that would put the twins about 30ish. About the right age for a war.....
177?A very big war....The Thirty are said to be wiped out in the war of the twins. For them to be completely destroyed, it would have to be a massive conflict. Something huge.
192 Banelion is born.At the time of Winter Warriors, Banelion is 72. This puts his birthday 228 years after the building of the Immortals home.
210?The Old King is a young prince.He is refered to as a "young prince" by Banelion when he was talking about "the first".
210?Banelion joins the army.I am assuming that Banelion joined the army at 18 as an Officer. From previous readings it is clear that the Drenai join the army at a young age.
221 The old king is still king at this point!Bison refers to having server the old king for 23 year. Therefore, at this point the old king must be in power still.....
221 Bison joins the army.Bison says he has served for 43 years since Winter Warriors.
229 Nogusta's family are murdered. He joins the army.He joined jsut after his family were murdered and has been serving for 35 years.
229 Prince Skanda is born.He is 35 during Winter Warriors.
244 Skanda become king at the age of 15.Bison says he has served the king for 20 years and his father 23 years before that.
264Winter WarriorsThe Drenai Army are occupying Ventria....This point is refered to in Narrative as being 300 years after the building of the Immortals Home.

Note 1

Please see my musings on the Barden and Angel Relationship for details and reasoning's on the placement of Barden's birth.