Three times: After the 2006, 2007 and 2009 seasons.
No. Tony Romo has always been a member of the Dallas Cowboys (2004-present).
The Dallas Cowboys have had three Super Bowl quarterbacks:Craig Morton (Super Bowl V).Roger Staubach (Super Bowls VI, X, XII and XIII).Troy Aikman (Super Bowls XXVII, XXVIII and XXX).
The Jacksonville Jaguars have Been to the playoffs once.
Tony Romo has won one playoff game in his career. The Dallas Cowboys beat the Philadelphia Eagles 34-14 on Saturday January 9, 2010. The Cowboys lost in the following round 34-3 against the Minnesota Vikings. He has played in playoff games in the the 2006-2007 and 2007-2008 playoffs, but the Dallas Cowboys lost both games.
They have been to the Stanley Cup finals 4 times and countless playoffs.
The Miami heat been in the NBA playoffs 4 times
Through the 2012 season, the San Diego Chargers made the playoffs 17 times.
Drew Bledsoe was the starting quarterback for the Dallas Cowboys in 2005 and 2006. Tony Romo replaced him midway through the 2006 season and has been the Cowboys' No. 1 quarterback ever since.