With all its intricate processes, colonialism, both as an ideology and a historical period, has been a rich source of inspiration for contemporary popular culture, whether in the form of movies, novels, digital games, or analogue games. This article presents a critical analysis of colonial representations in three examples of the latter: Puerto Rico ( 2002), Struggle of Empires ( 2004), and Archipelago ( 2012). These three games are simulation, strategy type Eurogames, with rules designed to emulate and reproduce two time periods: first-wave European colonialism ( Puerto Rico; Archipelago) and 18th-century European colonial expansion ( Struggle of Empires). On BoardGameGeek.com, where users have ranked more than 87,000 board games and extensions, these three are in the top three-hundred overall, with more than 3,000 votes each. Building on John McLeod’s definition of colonialism and interpretation of colonial economies, Edward Said’s theory of Orientalism, and Gayatri Spivak’s theory of subalternity, this comparative study examines representations of: a) the otherness of colonial subjects in relation to colonisers; b) indigenous peoples’ agency and subaltern voice; c) expressions of the indigenous culture; and d) Eurocentrism. The analysis investigates the denotative and connotative meanings of game rules, game mechanics, artwork, and tiles, critically assessing how these might influence the player’s cultural, social, and aesthetic experience of the ideological and historical context. In so doing, the article attempts to raise awareness about how these games (mis)represent colonial realities and relations.