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A gap in the strategic investment decision making process (SIDMP) literature shows little empirical research effectively distinguishing its effects on both context and culture. We used the 4-category contextual typology, developed from empirical SID research in Britain, U.S.A and Japan and further integrated cultural variables from the GLOBE studies using Singapore as our fourth more independent country research site. 18 decision makers from 9 Singaporean companies were interviewed. 3 Singaporean companies were matched equally across the primary, secondary & tertiary sectors to reflect contextual differences. The 4-category typology’s mapping depicts the 9 firms as Market Creators, Value Creators and Restructurers. Culturally, the 9 Singaporean firms scored highest for uncertainty avoidance, followed by power distance, future orientation, in group collectivism and assertiveness. Despite our small sample size, the clustering of the 3 matched firms in each contextual category indicates a larger contextual effect in contrast to cultural influences on the SIDMP.