That depends on what you mean by a winning season. If you mean the last time they had more wins than losses in the season, that would be 1996. If you mean the last time they won a bowl game, that was the 1985 Peach Bowl against Illinois.
The Pirates' last winning season was 1992.
The Rockies had their last winning season in 2007 when they went to the World Series and lost to the Boston Red Sox.
As of the 2007 season, the last time the two teams met was in the 1993 Sugar Bowl with Alabama winning 34-13.
2008
Had a winning season? 1997
Through the 2010 season, the Lions last winning season was 2000 when they went 9-7. The starting QB was Charlie Batch and the backup was Stoney Case.
Spain
2002. They were 10-6.
The last 16 is when they usually fail
Dublin's last winning of the Leinster Senior Football Championship was in 2014. Dublin's last winning of the Leinster Senior Hurling Championship was in 2013.
Through the 2008 season, Kentucky and Florida have met 59 times in football with Kentucky winning 17 times and Florida winning 42 times. The last time Kentucky beat Florida was November 15, 1986 in Lexington by the score of 10-3. Florida has won the last 22 meetings and 28 of the last 29.