This depends on the sport/event and cup. Either re-ask your question or see related answers.
Ottawa, eventually.
No, no they did not.
The Ottawa Hockey Club (nicknamed the Senators) first won the Stanley Cup in 1903 when it was a challenge cup.The current version of the Ottawa Senators has not won the Stanley Cup.
its not the Ottawa Rough Riders its the Saskatchewan Rough Riders and they won the cup in 2007-2008
the Ottawa senators won the Stanley cup 7 times and were given the name Ottawa senators in 1992
No Mexico have still to win a world cup.
The Ottawa Rough Riders defeated the Edmonton Eskimos to win the 1960 Grey Cup.
I believe you mean the Ottawa *Senators*, since there was never an NHL team called the Senders. Regardless, the modern Sens haven't ever won one.
No.
No
no
no