This depends on the sport and cup. Please see related questions or re-ask your question.
The New York Islanders, who won Stanley Cups from 4 Stanley Cups from 1980 to 1983.
University of Washington
The lakers
Barcelona they have won it 25 times
The New York Yankees did, actually going to four straight from 1998-2001.
It is not clear, it is Real Madrid.
the Boston Celtics because they have 17 cups
spain, 2010 italy, 2006 brazil, 2002 france, 1998
Brazil is the best having won 5 World Cups followed by Italy with 4 World Cups. Brazil last won the World Cup in 2002, Italy last won the World Cup in 2006.
The Montreal Canadians with 24 Cups. The team in second place is Toronto Maple Leafs with 13 Cups.
The Montreal Canadiens have won 24 Stanley Cups.
Edmonton Oilers - 5 (1984, 1985, 1987, 1988, 1990)