What if you'd held SPXX?
A $1,000 investment in Nuveen S&P 500 Dynamic Overwrite Fund (SPXX) at the month-end close of 2005-11 would be worth $4,790 at the close of 2026-08 — +379.0% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $6,169.
Your scenario
Result
If you'd bought $1,000 at the start of each year
Value of $1,000 invested on January 1 of each year, held to 2026-08, dividends included.
Every year, $1,000 from 2005
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2005 | $1,000 | — |
| 2006 | $1,226 | +22.6% |
| 2007 | $1,183 | -3.5% |
| 2008 | $826 | -30.1% |
| 2009 | $1,113 | +34.7% |
| 2010 | $1,278 | +14.8% |
| 2011 | $1,217 | -4.8% |
| 2012 | $1,423 | +16.9% |
| 2013 | $1,684 | +18.3% |
| 2014 | $1,835 | +9.0% |
| 2015 | $1,864 | +1.6% |
| 2016 | $2,142 | +14.9% |
| 2017 | $2,739 | +27.9% |
| 2018 | $2,371 | -13.4% |
| 2019 | $2,974 | +25.4% |
| 2020 | $2,962 | -0.4% |
| 2021 | $3,823 | +29.1% |
| 2022 | $3,557 | -7.0% |
| 2023 | $3,588 | +0.9% |
| 2024 | $4,559 | +27.1% |
| 2025 | $5,009 | +9.9% |
| 2026 | $5,554 | +10.9% |
Best and worst month-end to buy
The best single month-end close to have bought SPXX was 2009-02 ($2.45): $1,000 then is $7,820 today. The worst was 2026-08 ($19.16): $1,000 then is $1,000.
FAQ
What would $1,000 in SPXX be worth today?
A $1,000 investment in Nuveen S&P 500 Dynamic Overwrite Fund (SPXX) at the start of 2005 would be worth about $4,790 today, a total return of +379.0%. Dividends are reinvested in these figures.
What were the best and worst years for SPXX?
Nuveen S&P 500 Dynamic Overwrite Fund (SPXX)'s strongest calendar year since 2005 was 2009, a +34.7% return — $1,000 held through that year became about $1,347 by year-end. Its weakest year was 2008, at -30.1%.
Does the calculator include dividends and splits?
Yes where available. Prices are adjusted for both stock splits and reinvested dividends (total return), the same measure brokerages use.
How much would $100 per month in SPXX have grown?
Investing $100 at the end of every month since 2005-11 would have grown to about $77,212 on $25,000 invested.
Did SPXX beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $6,169. SPXX trailed the S&P 500 by +22.4% in total return.
Is this investment advice?
No. Wall Street Regrets is an entertainment and education tool. Every number is a historical calculation, not a prediction, and past performance never guarantees future results.
Methodology
Nuveen S&P 500 Dynamic Overwrite Fund (SPXX) historical total-return data from 2005-11 to 2026-08, reduced to month-end closes for the tables above.
Returns use adjusted close prices from Yahoo Finance historical data — adjusted for stock splits and reinvested dividends — the same convention used by major brokerages. A "year" scenario invests $1,000 at the prior December's month-end close and values it at the latest available month-end close. Non-USD amounts are converted at historical month-end exchange rates (Yahoo Finance): to USD on the buy date and back to your currency at the latest rate, so the return reflects the currency move as well as the asset.
Month-end resolution means intra-month extremes are not captured in tables; the calculator uses exact trading-day closes where daily data is available. Figures ignore taxes, fees, and the currency effects of non-USD listings. History is not a forecast. Wall Street Regrets is entertainment, not investment advice.
What if you'd held…
Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.