The article examines cross-border cooperation between organizations engaged in the enterprise sector in the bordering regions across Europe, with the main goal of noting the benefits and obstacles that such cooperation brings to the business sector and regions. In total, 32 articles that examines empirical case studies from the semistructured literature review were extracted and presented. The results show that there are eight main groups of factors that have a significant impact on the crossborder cooperation among enterprises; those are language and sociocultural barriers; perceptions and attitudes toward neighbours; institutional and legal barriers; weak market conditions and structural limitations; enterprise motivation and benefits; innovation and knowledge transfer; entrepreneurship and social enterprise; and project governance and policy influence.