Nov. 4 (Bloomberg) -- New York Yankees fans who invest in the stock market may find conflict between a World Series title and a happy holiday season.

The Yankees, seeking their 27th championship, lead the Philadelphia Phillies three games to two in the best-of-seven matchup. Game 6 is tonight at Yankee Stadium and a seventh game would be held there tomorrow if necessary.

The CHART OF THE DAY compares the historical November and December performance of the S&P 500 Index, the benchmark index for American equities, when the Yankees lose in the World Series to when they win the title.

Since the S&P 500 began trading in 1928, it has averaged 3 percent returns for those two months following the Yankees’ 10 World Series defeats; 2.16 percent returns in the 24 years they won the title; and 0.9 percent returns when the Yankees didn’t make the World Series at all. The market does best when New York reaches the World Series -- and loses.

“All you guys that root for anybody but the Yankees, you’re right,” said Soleil Securities Corp. Chief Investment Officer Vince Farrell, a Bronx, New York, native and Yankees fan. “The Yankees lose, the market does better. Everybody hates the Yankees, so you’re so happy that they’ve lost, and you look at the world with rose-colored glasses.”

Two of New York’s previous 26 championships, in 1923 and 1927, came before the creation of the S&P 500.

Each World Series game at Yankee Stadium is worth $15.5 million to the New York City economy, according to an estimate by the city’s Economic Development Corp.

First Meeting

New York swept the Phillies in the teams’ only other World Series matchup in 1950, a championship that was followed by 2.9 percent returns for the S&P 500 that November through December.

Since then, December has been the best overall month for the index, with 1.64 percent average gains, followed by a tie between November and April (when Major League Baseball’s season begins) at 1.5 percent, according to Bloomberg data.

While the end of the year may or may not bring what’s called a Santa Claus rally on Wall Street due to holiday effects such as bonuses and tax considerations, the Steinbrenner family, which owns the Yankees, has been giving the team’s fans the gifts of high-priced free agents for years.

This season, they gave multiyear contracts to pitchers CC Sabathia and A.J. Burnett, and added All-Star first baseman Mark Teixeira for a total contract value of $423.5 million. The franchise’s opening day payroll was $210 million, the biggest in baseball.

No Playoffs

Without those players, the Yankees missed the playoffs in 2008. The S&P 500 fell 6.52 percent over the final two months.

The Phillies did make the postseason, capturing their first championship in 28 years with a five-game World Series win over the Tampa Bay Rays. The S&P 500 rose 5.2 percent in 1980 following the Phillies’ first title.

Phillies’ fan Michael O’Rourke, who is chief market strategist at Yardley, Pennsylvania-based BTIG LLC, said he’d prefer not to see a complete replay of last year’s developments.

Asked how he’d react if a Phillies’ repeat means another Wall Street slump during the holiday season, O’Rourke said, “I will go out and buy a Yankees cap.”

To contact the reporter on this story: Mason Levinson in New York at mlevinson@bloomberg.net.

Last Updated: November 4, 2009 00:00 EST