Canada's first experience with separation occurred in 1868, less than 1 year after it's birth.

Joseph Howe, from Nova Scotia, was a dyed-in-the-wool imperialist who never accepted the terms of confederation of Canada.  He believed that Atlantic Canada was better ruled by Britain than by the "rabble" from Ottawa.

Canada was "borne" on July 1, 1867 when it's first Parliament was sworn in.   On November 6, 1867 the first Speech From the Throne was read.  Everything looked rosy for the new country but under the surface a little discontent grew.

Howe had not given up his opposition to the Canadian Union... quite the opposite, he was giving impassioned speeches directed at the repeal of the Union.

In 1868, Howe led a Nova Scotian delegation to London to petition the imperial Parliament to release Nova Scotia from the their commitment to Canada.

Their request was denied by the British government of Benjamin Disreali.

Was Howe surprised by the answer he received?  I hope not.  After all, Disreali was one of the authors of the British North America Act which created Canada.

Thus was Canada's first brush with separation.