For almost 30 years, the Stanley Cup has been long overdue on Canadian soil and if a team from the country looks to fill the gap, the next few days could be crucial.

The National Hockey League (NHL) trade deadline is 3 p.m. Friday, and some clubs have already taken steps to improve their chances of a long road to the playoffs. This is also the case with the Toronto Maple Leafs, second in the Atlantic Division, who recently signed veteran Ryan O’Reilly an important part of the St. Louis Blues championship in spring 2019. On Monday they brought the forward to Sam Lafferty and guard Jake McCabe from the Chicago Blackhawks.

Now general manager Kyle Dubas has left the door open to more changes through Friday. Also, will he want to start the playoffs with Ilya Samsonov and Matt Murray as goalies? The answer may come soon.

“How can we compete better? Because just having fun is not enough for us. It’s time to win,” he told media on Monday at a news conference.

Hypocrite or wannabe?

In the Western Conference, the Edmonton Oilers can count on Connor McDavid and Leon Draisaitl on offense, but they’ll need additional tools to earn top honors. Several observers believe that GM Ken Holland must seize the opportunity to capitalize on the two players’ prime years before and improve his roster very quickly. The club has been rumored to be linked to defenders Joel Edmundson (Montreal Canadiens), Jakob Chychrun (Arizona Coyotes) and Mattias Ekholm (Nashville Predators) in recent days.

“As the deadline approaches, when your team is playing at a high level, you definitely want to try your luck as a coach,” Holland recently told reporters.

Finally, on the side of the Winnipeg Jets, holders of the first pass of the clubs drafted from the west, the echoes are similar. Despite some recent troubles, the Manitoba lineup has the potential to do some damage, thanks in particular to Connor Hellebuyck, Pierre-Luc Dubois, Kyle Connor, Josh Morrissey and Mark Scheifele. Will GM Kevin Cheveldayoff be active? His players seem to want it.

“It’s really an important phase on the eve of the deadline and you want to prove that your team is part of the buy-side. I think we’ve achieved that so far, but we have to keep going like this,” center Adam Lowry told Sportsnet.

– The 1993 Canadiens were the last team in the country to win the cup. The Oilers have waited since 1990, while the Calgary Flames got it the previous year for the only time in franchise history. The Jets never won the title, as did the Vancouver Canucks and the contemporary iteration of the Ottawa Senators. As for the Leafs, their most recent conquest remains that of 1966-1967, the final season to feature only the NHL’s six original formations.