This study presents a rigorous exploration of the effects of single versus multiple M&A deals on the performance of acquiring firms. A pooled ordinary least squares (OLS) regression analysis was employed to examine our key performance indicators: Value at Risk (VaR), Value of Return (VoR), and Returns across year, month, and week time frames. Findings reveal that multiple M&A deals can enhance stock performance and VoR, while also increasing VaR, indicating higher potential for downside risk. This research enriches the M&A literature by focusing on the differential impacts of single and multiple acquisitions on these crucial financial metrics. Its insights guide firms and investors in understanding the delicate interplay between the number of acquisitions, prospective gains, and related risks.