Here is the full list of all 28 Massive Chalice achievements.
Completed the game on Normal Difficulty
Took at least 3 of your 5 initial Vanguard Bloodlines all the way to the Final Battle
Survived 300 years (Reached year 301)
Killed 5 or more enemies with a drunk hero in one tactical battle
Survived 150 years (Reached year 151)
Kill 4 or more enemies with one attack
Adopted multiple children into the same Keep
Received your first Relic
Appointed a Standard
Survived 50 years (Reached year 51)
Deployed a Vanguard of 5 different classes
Killed an enemy with a Burst Bush
Appointed a Sagewright
Your first hero came of age
The first baby was born
Arranged your first Marriage
Defended your first Keep
Completed the game on Hard Difficulty
Completed the game on Brütal Difficulty
Completed an IRON game (any Difficulty)
Completed an IRON game (Brütal Difficulty)
Built a building in every Region
Beat a tactical battle where every hero is over 60 years old
Beat a tactical battle without taking any damage
Progressed a Relic to its maximum level
Deployed a Vanguard with only Cadence Weapons, Armor, and Items
Killed 50 or more enemies with one hero
Defeated an enemy from the past