In Glen More II: Chronicles, each player represents the leader of a Scottish clan, from the early Middle Ages to the 19th century. As a clan leader, you try to expand your territory and wealth by making the right decisions at the right time. This can be done by creating pastures for cattle, growing barley for whisky production, trading goods at various markets, or gaining control over important locations such as lochs and castles.

The game plays out over four rounds, with each round represented by a deck of tiles. After each round, there is a scoring phase, where players compare their whisky barrels, Scottish clansmen in their home stronghold, map cards, and characters to the player with the least in each category. Victory points are awarded based on the relative difference. After four rounds, additional points are awarded for gold coins and certain locations, while penalty points are given for territory size, by comparing it to the smallest area in the game.

The core mechanics of Glen More II: Chronicles remain the same as in the original Glen More : the last player on the time track takes a tile and may advance as far as they wish. After paying the cost, the tile is placed in the territory, where it activates itself and all adjacent tiles. This triggers the production of resources, movement points, victory points, and other effects. Then it is the turn of the player who is at the back again.

The "Chronicles" of the title are a major new element in this edition, consisting of eight expansions that add additional gameplay elements. Each Chronicle introduces a unique mechanic. For example, the Highland Boat Race Chronicle tells the story of a boat race, in which players must navigate their boat along the rivers of all other players in order to reach their home fortress first. The Hammer of the Scots Chronicle adds a neutral "Englishman" piece to the time track, which players can control to gain an extra turn—provided they can pay for him via the market system. All of the Chronicles can be combined as desired, although designer Matthias Cramer recommends using only one or two at a time unless you want to play an extremely extensive game.

Another big change in this edition is the ability to invest in famous Scottish figures, represented by a new type of "person" tile. These figures not only have their own scoring mechanic, but also trigger one-time or ongoing effects on the tactical clan board. This adds an extra layer of strategic choice, especially since the ongoing effects allow players to develop a unique personal strategy through the clan board.