As a multilingual system,Wikipedia provides many challenges for academics and engineers alike. One such challenge is cultural contextualisation of Wikipedia content, and the lack of approaches to effectively quantify it. Additionally, what seems to lack is the intent of establishing sound computational practices and frameworks for measuring cultural variations in the data. Current approaches seem to mostly be dictated by the data availability, which makes it difficult to apply them in other contexts. Another common drawback is that they rarely scale due to a significant qualitative or translation effort. To address these limitations, this thesis develops and tests two modular quantitative approaches. They are aimed at quantifying culture-related phenomena in systems which rely on multilingual user-generated content. In particular, they allow to: (1) operationalise a custom concept of culture in a system; (2) quantify and compare culture-specific content- or coverage biases in such a system; and (3) map a large scale landscape of shared cultural interests and focal points. Empirical validation of these approaches is split into two parts. First, an approach to mapping Wikipedia communities of shared co-editing interests is validated on two large Wikipedia datasets comprising multilateral geopolitical and linguistic editor communities. Both datasets reveal measurable clusters of consistent co-editing interest, and computationally confirm that these clusters correspond to existing colonial, religious, socio economic, and geographical ties. Second, an approach to quantifying content differences is validated on a multilingual Wikipedia dataset, and a multi-platform (Wikipedia and Encyclopedia Britannica) dataset. Both are limited to a selected knowledge domain of national history. This analysis allows, for the first time on the large scale, to quantify and visualise the distribution of historical focal points in the articles on national histories. All results are cross-validated either by domain experts, or external datasets. Main thesis contributions. This thesis: (1) presents an effort to formalise the process of measuring cultural variations in user-generated data; (2) introduces and tests two novel approaches to quantifying cultural contextualisation in multilingual data; (3) synthesises a valuable overview of literature on defining and quantifying culture; (4) provides important empirical insights on the effect of culture on Wikipedia content and coverage; demonstrates that Wikipedia is not contextfree, and these differences should not be treated as noise, but rather, as an important feature of the data. (5) makes practical service contributions through sharing data and visualisations.