KEY vs MSFT: KeyCorp vs Microsoft Corporation Historical Returns & Investment Comparison

This KEY vs MSFT comparison analyzes the historical stock performance of KeyCorp and Microsoft Corporation side-by-side. Using real, adjusted market data, this tool shows how identical investments in both stocks would have performed over time—highlighting differences in returns, volatility, and consistency across market cycles.

Use the interactive calculator below to adjust the investment amount and time period, visualizing how KeyCorp and Microsoft Corporation have historically performed against each other.

Compare Stock Performance

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Performance Summary

$10,000 invested from 1987 to 2025 (39 years)

Head-to-Head Record

16
KEY Wins
0
Ties
23
MSFT Wins

Over the 39-year comparison period, KeyCorp outperformed Microsoft Corporation in 16 years, while Microsoft Corporation outperformed KeyCorp in 23 years.

KEY - KeyCorp

Average Annual Return:+11.58%
Best Year:+100.33% (1991)
Worst Year:-60.45% (2008)
Win Rate:56.4% (22/39 years)
Total Value:$128,926.97
Total Gain:+$118,926.97 (+1189.27%)

MSFT - Microsoft Corporation

Average Annual Return:+31.68%
Best Year:+127.22% (1987)
Worst Year:-62.79% (2000)
Win Rate:77.5% (31/40 years)
Total Value:$63,781,897.96
Total Gain:+$63,771,897.96 (+637718.98%)

Overall Winner: MSFT with an average annual return of 31.68% (vs 11.58% for KEY)

Understanding KEY vs MSFT Performance

When comparing KeyCorp and Microsoft Corporation, investors should consider multiple factors beyond just total returns. Volatility, consistency of growth, dividend payments, and sector-specific risks all play crucial roles in determining which stock might be better suited for your investment strategy and risk tolerance.

Historical performance data shows how each stock responded to market downturns, economic expansions, and company-specific events. While past performance doesn't guarantee future results, understanding these patterns can help inform investment decisions and portfolio allocation strategies.

Cumulative Growth Comparison

A $10,000 investment in KeyCorp grew to $128,927, compared to $63,781,898 for Microsoft Corporation over the same period.

Year-by-Year Comparison

YearKEY ReturnKEY CumulativeMSFT ReturnMSFT CumulativeDifferenceWinner
1987 (Start)-$10,000.00-$10,000.00-Initial Investment
1988-2.69%$9,730.51+127.22%$39,155.81-129.92% (MSFT)MSFT
1989-3.77%$9,363.68-4.91%$37,233.03+1.14% (KEY)KEY
1990+38.49%$12,967.37+62.24%$60,406.07-23.75% (MSFT)MSFT
1991-5.39%$12,268.39+69.58%$102,435.17-74.97% (MSFT)MSFT
1992+100.33%$24,576.71+123.24%$228,680.64-22.92% (MSFT)MSFT
1993+37.88%$33,887.44+12.34%$256,889.66+25.55% (KEY)KEY
1994-5.76%$31,935.04-5.29%$243,309.53-0.48% (MSFT)MSFT
1995-9.81%$28,802.04+52.57%$371,227.53-62.38% (MSFT)MSFT
1996+50.52%$43,353.25+45.79%$541,228.97+4.73% (KEY)KEY
1997+43.01%$62,001.12+84.12%$996,524.76-41.11% (MSFT)MSFT
1998+46.13%$90,603.67+58.35%$1,577,958.22-12.21% (MSFT)MSFT
1999-6.33%$84,866.35+111.53%$3,337,930.90-117.87% (MSFT)MSFT
2000-27.93%$61,167.09+65.60%$5,527,711.79-93.53% (MSFT)MSFT
2001+42.75%$87,316.68-62.79%$2,056,960.51+105.54% (KEY)KEY
2002-5.93%$82,142.80+52.74%$3,141,755.21-58.66% (MSFT)MSFT
2003+7.40%$88,220.29-22.88%$2,422,863.26+30.28% (KEY)KEY
2004+18.52%$104,561.77+2.80%$2,490,701.94+15.72% (KEY)KEY
2005+21.33%$126,860.76+8.81%$2,710,135.61+12.52% (KEY)KEY
2006+2.41%$129,924.13-1.01%$2,682,698.63+3.43% (KEY)KEY
2007+17.26%$152,352.88+12.86%$3,027,729.87+4.40% (KEY)KEY
2008-35.51%$98,258.34+20.84%$3,658,796.67-56.35% (MSFT)MSFT
2009-60.45%$38,859.46-43.79%$2,056,771.16-16.67% (MSFT)MSFT
2010-36.61%$24,634.43+53.44%$3,155,957.24-90.05% (MSFT)MSFT
2011+49.80%$36,901.84-7.94%$2,905,242.80+57.74% (KEY)KEY
2012-13.93%$31,761.88-4.75%$2,767,111.96-9.17% (MSFT)MSFT
2013+10.82%$35,197.68+2.60%$2,838,991.28+8.22% (KEY)KEY
2014+55.82%$54,844.37+39.54%$3,961,633.63+16.27% (KEY)KEY
2015+6.56%$58,443.97+28.42%$5,087,641.85-21.86% (MSFT)MSFT
2016-2.83%$56,788.57+21.88%$6,200,739.95-24.71% (MSFT)MSFT
2017+44.66%$82,151.12+16.51%$7,224,217.07+28.16% (KEY)KEY
2018+12.80%$92,664.91+39.74%$10,095,202.03-26.94% (MSFT)MSFT
2019-24.61%$69,860.94+20.22%$12,136,360.37-44.83% (MSFT)MSFT
2020+40.44%$98,112.65+58.26%$19,206,911.25-17.82% (MSFT)MSFT
2021-14.59%$83,802.25+39.94%$26,878,701.70-54.53% (MSFT)MSFT
2022+47.00%$123,186.07+55.79%$41,874,319.16-8.79% (MSFT)MSFT
2023-23.18%$94,628.51-27.69%$30,280,494.98+4.50% (KEY)KEY
2024-12.48%$82,818.65+58.35%$47,949,092.29-70.83% (MSFT)MSFT
2025+23.54%$102,316.81+14.50%$54,902,457.42+9.04% (KEY)KEY
2026+26.01%$128,926.97+16.17%$63,781,897.96+9.83% (KEY)KEY

Annual returns include dividends and stock splits. Cumulative values show growth of $10,000 invested from the first year. Positive difference means KEY outperformed MSFT that year.

Company Profiles

1

KeyCorp

KEY

KeyCorp operates as the holding company for KeyBank National Association, providing various retail and commercial banking products and services in the United States. It serves individuals, small businesses, and corporations with a range of financial solutions, including deposit accounts, lending, wealth management, and investment services.

Key Innovations

  • A long-standing history of adapting to and evolving with the financial landscape, continuously offering relevant banking products and services for nearly two centuries.
  • Providing a comprehensive suite of financial solutions that cater to the diverse needs of both individual consumers and complex commercial clients, fostering strong client relationships.
  • Balancing a commitment to community banking with the capacity to serve larger commercial entities, demonstrating versatility and a broad market reach.

Business Segments

  • Consumer Banking
    Offers a comprehensive suite of banking products and services to individual consumers, including checking and savings accounts, credit cards, mortgages, and personal loans.
  • Commercial Banking
    Provides financial solutions to businesses of all sizes, from small enterprises to large corporations, encompassing commercial loans, treasury management, and investment banking services.
2

Microsoft Corporation

MSFT

Microsoft Corporation is a global technology powerhouse that develops, licenses, and supports a wide range of software products, services, and devices. As of 2026, the company has successfully transitioned into an 'AI-first' organization, leveraging its strategic partnership with OpenAI to integrate generative AI across its entire tech stack. Microsoft is the dominant provider in enterprise computing through its Windows operating system and Office productivity suite, and it is a leading player in the global cloud market with Azure. Its business model centers on digital transformation, cloud infrastructure, and the emerging economy of autonomous AI agents.

Key Innovations

  • Azure AI Services & Copilot Ecosystem
  • Windows 11 and Next-Gen 'Copilot+' AI PC architecture
  • Microsoft 365 Copilot (Generative AI for productivity)
  • HoloLens and Mixed Reality (Industrial Metaverse)
  • Custom Silicon: Azure Maia AI Accelerator and Azure Cobalt CPU
  • Topological Quantum Computing (Majorana 1 chip)
  • Agentic AI: Autonomous digital coworkers built on Copilot Studio

Business Segments

  • Intelligent Cloud
    The company's primary growth engine, consisting of public, private, and hybrid server products and cloud services. Key offerings include Azure—a comprehensive cloud platform for computing, networking, and AI—as well as SQL Server, Windows Server, GitHub, and Nuance Healthcare. In 2026, this segment is heavily focused on scaling AI 'superfactories' and providing the infrastructure for large-scale generative AI workloads.
  • Productivity and Business Processes
    Focuses on productivity, communication, and information services. It includes Microsoft 365 (formerly Office), which has evolved into a Copilot-integrated subscription service for both commercial and consumer users. This segment also encompasses LinkedIn (talent and marketing solutions), Dynamics 365 (cloud-based ERP and CRM), and the Microsoft Power Platform for low-code development and hyperautomation.
  • More Personal Computing
    Encompasses products and services geared toward end-users and developers across devices. This includes Windows OEM and commercial licensing, Surface devices, Search and news advertising (Bing and Copilot), and Gaming. Following the acquisition of Activision Blizzard, the Gaming division includes Xbox hardware, content, and services like Game Pass, making Microsoft one of the largest video game publishers globally.

How This Comparison Works

Our stock comparison tool uses adjusted closing prices to calculate year-by-year returns for both stocks. This ensures an apples-to-apples comparison that accounts for:

  • Dividends: All dividend payments are reinvested
  • Stock splits: Historical prices are adjusted for all splits
  • Head-to-head record: Shows which stock outperformed each year
  • Statistical analysis: Average returns, best/worst years, and win rates

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Important Disclaimer

This comparison tool is for educational and informational purposes only and does not constitute financial, investment, or trading advice. Past performance is not indicative of future results. Historical returns include dividends and stock splits but do not account for taxes, fees, inflation, or individual circumstances. Stock market investments carry risk, including the potential loss of principal. Always consult with a qualified financial advisor before making investment decisions. The data presented is based on historical market data and may contain inaccuracies or delays.