MSFT’s worst drop since 1999 was 69%
Microsoft (MSFT) fell 69% from Dec 1999 to Mar 2009. It took 14.5 years from that peak to close at a new high, in Jul 2014. Over the same years the S&P 500 fell as much as 55%.
That drop is milder than most. It ranks 560th of the 986 stocks PortfolioAutopsy tracks, counted from the deepest.
Drawdown from the last high, 1999 to now
How MSFT held up in each crash
| Crash | Years | MSFT | S&P 500 |
|---|---|---|---|
| Dot-com bust | 2000–02 | −64.4% | −47.5% |
| Financial crisis | 2007–09 | −57.9% | −55.2% |
| COVID crash | 2020 | −28.0% | −33.7% |
| 2022 rate shock | 2022 | −35.7% | −24.5% |
Each number is the deepest fall from a high inside that window, using daily prices with dividends reinvested.
See how MSFT behaves inside your whole mix, with the worst 12 months, loss odds and crash replays. Free, no signup, and the math runs in your browser.
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What was MSFT’s maximum drawdown?
MSFT’s deepest fall since 1999 was 69.4%, from its high on December 27, 1999 to its low on March 9, 2009. The figure uses daily prices with dividends reinvested.
How long did MSFT take to recover?
14.5 years. MSFT first closed above its Dec 1999 high again on July 16, 2014.
Was MSFT riskier than the S&P 500?
Over the same years, MSFT’s worst drop was 69.4% against 55.2% for the S&P 500 (SPY), and its worst 12 months were −64.7% against −47.4%.
Compare with
Daily adjusted closes from Yahoo Finance, January 5, 1999 through October 13, 2026, dividends reinvested. Historical facts, not a forecast and not investment advice.