Editor's note: NESN.com is teaming up with WhatIfSports.com to crown the greatest Red Sox team of all time with the "Red Sox Showdown for the Ages." For more information on the 16-team tournament, click here.
The 1999 Red Sox couldn't pull off a second straight upset in the second round of the "Red Sox Showdown for the Ages." One week after knocking off the top-seeded 2004 team, the 1999 squad fell victim to a very dangerous 2008 bunch.
Would the 2008 Red Sox defeat the 1999 Red Sox?survey software
