Following two disappointing late regular season collapses, the Boston Bruins face another off-season of uncertainty as they try to somehow improve their club for 2016-17. Regardless of how the Black and Gold will look a few months from now, the schedule release is always a time to circle important dates in the upcoming season.

Highlighted by three straight road games to start the year, a Thanksgiving matchup in Ottawa, 14 sets of back to back games and eight of their final 10 regular season contests at TD Garden, the Bruins will have their work cut out for them in hopes of returning to the postseason.

Trying to get this list to five with nearly four months until the start of the upcoming campaign was pretty difficult. With that in mind, here is an early look at five Bruins games to watch in 2016-17.

Thursday, October 20 vs. Devils

The Bruins welcome Corey Schneider and the Devils for their home opener on October 20th. (Photo by Joe Makarski, Bruins Daily)

Exactly a week after they open the season in Columbus, the Bruins welcome the Devils for their first home game of the season. This will be fresh off a three-game road trip, which also includes stops in Toronto and Winnipeg, to start the season.

The change of pace could be a good thing for the Bruins as they hope to establish an identity away from Causeway Street before returning home (a story for another day).

Saturday, October 22 vs. Canadiens

The Canadiens return to the Commonwealth for the first time since the Winter Classic in late October. (Photo by Joe Makarski, Bruins Daily)

The first Bruins-Habs meeting of 2016-17 will also mark Montreal’s first appearance in the Massachusetts Commonwealth since steamrolling the Black and Gold this past New Year’s Day at Gillette Stadium. With Carey Price expected to be healthy in time for the start of the new season, the Bruins will likely have their work cut out for them in hopes of trying to snap an eight-game regular season home losing streak against their hated rivals.

Wednesday, December 14 at Penguins

Brad Marchand and travel to Pittsburgh for their first meeting of the season against the champs in Mid-December. (Photo by Joe Makarski, Bruins Daily)

It’s been a week after their fourth Stanley Cup win in franchise history, and it’s still pretty astonishing to see the progression of the Penguins during the course of 2015-16. This is the same Penguins squad that the Bruins swept in three meetings against Phil Kessel, Sidney Crosby, Evgeni Malkin and company.

The Bruins get their first shot at the champs 11 days before Christmas. Will their success against the Pens carry over into next season?

Sunday, February 26 at Stars

The Bruins pay a visit to old friend Tyler Seguin in Dallas on February 26th — two days before the NHL Trade Deadline. (Photo by Joe Makarski, Bruins Daily

Fresh off winning the Central Division and advancing to the second round a year ago, the Stars have the tools in place to make another run next season. This late season matchup against Tyler Seguin, Jamie Benn and company is the last Bruins game before the trade deadline, which takes place February 28th. How the Bruins look after the deadline is anyone’s guess, but depending on circumstances, this could prove to be an interesting afternoon for the franchise in ‘Big D.’

Saturday, March 11 vs. Flyers

A late season showdown with the Flyers could help dictate the Bruins’ playoff fate in 2016-17. (Photo by Joe Makarski, Bruins Daily)

For two straight years, the Bruins were knocked out of the top-8 by a team that made an improbable run. Last year the Flyers overtook the Bruins for the final wild card spot on the last day of the season. Who knows what path(s) these two teams will take in 2016-17, but if history repeats itself, this could be one of the most important Bruins’ games of the year.