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Despite being acknowledged as the primary catalyst for economic development, entrepreneurship in emerging markets contends with multiple constraints. The availability of unexploited business opportunities certainly raises the entrepreneurial potential of Small and Medium Enterprises (SMEs). Entrepreneurial orientation strategy strongly supports SMEs to improve their position in the market by instilling the courage to explore new prospects and take risks, promote innovation, act proactively on the market, and establish autonomy and competitive aggressiveness as norms in their operations. This research focuses on the entrepreneurial orientation approach as a key firm-level phenomenon and its influence on business performance in emerging markets. More specifically, the study elaborates on SMEs’ risk-taking, innovativeness, pro-activeness, autonomy, and competitive aggressiveness under the moderating influence of unexploited opportunities. A multiple-case study technique was used to develop the five propositions generated from the conceptual framework of the study. Six companies operating in the private healthcare sector in North Macedonia actively participated in the research, contributing a substantial body of data. According to the study findings, the unexploited opportunities have a reasonably large effect on SMEs’ entrepreneurial orientation activities and corresponding performance. Nonetheless, despite the hostile entrepreneurial environment, SMEs have demonstrated boldness in taking risks, initiating innovation, and continuity in taking proactive actions in the private healthcare industry.