What If You Had Invested in Microsoft 10 Years Ago?

MSFT: all at once or every month?

Take $12,000: all of it on day one, or $1,000 a month for a year. Across every starting month since 1986 (477 of them), the lump sum was ahead after 12 months in 356 (75%). The lump sum usually won, but roughly one start in 4 favored spreading it out. The best case for monthly investing was a start in March 2000, when it finished the year 65% ahead.

Worst drop

MSFT's worst fall in this history was -66.7%, a loss of more than half, from December 1999 to February 2009. Getting back to the old high took until July 2014: 65 months from the bottom and 14.6 years from the peak. $1,000 invested at that peak shrank to about $333 at the low.

Microsoft dividends

MSFT paid $3.64 per share over the last 12 months, quarterly. At $535.93 that is 0.68%, a small yield; nearly all of the return has come from the price. From 2020 to 2025 the yearly payout grew +10.2% a year, well ahead of inflation. The yearly total did not fall once in the last ten years. Amounts are adjusted for splits.

Yield = each year’s dividends divided by the price at the end of the year.

MSFT dividend history: last 12 payments

Stock splits

• September 1987: 2-for-1
• April 1990: 2-for-1
• June 1991: 1.5-for-1
• June 1992: 1.5-for-1
• May 1994: 2-for-1
• December 1996: 2-for-1
• February 1998: 2-for-1
• March 1999: 2-for-1
• February 2003: 2-for-1

One share bought before 1987 is 288 shares today.

About Microsoft

Microsoft dominated the 1990s with Windows and Office, then spent more than a decade going nowhere: its share price did not regain its 1999 high until 2016, and even with dividends reinvested it took until 2014. The turnaround came with the shift to cloud computing under Satya Nadella, who became CEO in 2014, with Azure and Office 365 subscriptions.

That flat decade is a good test for the what-if calculator. $1,000 invested at the end of 1999 shows how long even a great company can take to recover from an overvalued starting price, and how much monthly investing through the slump helped.

Microsoft started paying a dividend in 2003 and paid a one-time special dividend of $3 a share in 2004. It has raised the regular dividend every year since.

How the business changed

Microsoft today earns most of its money from businesses that barely existed in 2010: Azure cloud computing, Office 365 subscriptions, LinkedIn, and gaming, which grew much larger with the purchase of Activision Blizzard in 2023 for about $69 billion. Selling software as a subscription instead of in boxes made its revenue steadier and helped the stock re-rate.

A steady dividend grower

Microsoft's yield is under 1% because the share price has grown so much, but it has raised its dividend every year for more than twenty years. It is one of the few large technology companies that pays a meaningful, growing dividend, which is why it shows up in dividend-growth ETFs such as VIG and DGRO as well as in growth funds.

Questions about MSFT

How much would $10,000 invested in MSFT 20 years ago be worth today?

About $259,687 with dividends reinvested, invested at the November 2006 close: 2496.9% in total, or 17.7% a year.

When does MSFT pay dividends?

In the last 12 months the payments went out in February, May, August and November, $3.64 per share in total.

Did MSFT beat the S&P 500?

Yes. Over the last 20 years it was ahead by 7.1 percentage points a year: +17.7% a year for MSFT against +10.6% for SPY, dividends reinvested. It also fell harder at its worst (-66.7% against -50.8% for SPY over the same history).