As one of the world’s major enterprises, Microsoft has historically strengthened its market position by strategically leveraging acquisitions to navigate the changing market land- scape. This article examines the impact of four major acquisitions in two industries, including gaming (Activision Blizzard, ZeniMax Media) and telecommunications (Nokia, Skype), on Mi- crosoft’s stock price. The work uses case study and event study analysis to investigate acquisition motivations, timelines, and stock market performance in the gaming and telecommunications industries, using market models of returns and buy-and-hold ratio analysis. Our findings indicate that acquisitions in the gaming industry yield more positive and consistent stock performance compared to those in the telecom sector. Specifically, Activision Blizzard’s acquisition demon- strated strong long-term cumulative abnormal returns, while Nokia’s acquisition immediately led to an adverse market reaction. Our study suggests that Microsoft should acquire better indus- tries from these high-profile acquisitions to guide Microsoft’s future growth. These acquisitions bring corresponding developments to Microsoft’s later development and provide enlightening suggestions for other companies and enterprises.