That time the Stanley Cup final would include the Canucks or Leafs
It wasn't a classic hockey rivalry, but Vancouver had plenty of pent-up hostility against Toronto when the Canucks and the Leafs met in the 1994 NHL playoffs.
When the CRTC decided the internet couldn't be regulated
It took almost a year of study, but in the end the Canadian broadcast regulator decided it wasn't its place to enforce rules for audio and video online in 1999.
When Toronto's mayor planned to make Yonge and Bay one-way streets
Mayor Art Eggleton had an idea to address traffic flow in downtown Toronto, but it got no buy-in from merchants on the two city streets.