After a 2018-19 season where the Winnipeg Jets fell apart down the stretch and got bounced from the playoffs early, they will look to get back on track in 2019-20 and prove wrong those who feel their window to contend for the Stanley Cup has shut.

There’s considerably less hype in Winnipeg and in the media for the upcoming season — now less than a month away — than a year ago, when many thought the Jets could conquer all comers. Summer was tough on the team, too: Ben Chiarot, Tyler Myers, Brandon Tanev, and Jacob Trouba all departed for greener pastures. Add to that Kyle Connor and Patrik Laine, who remain unsigned and don’t seem ready to put pen to paper anytime soon, and one can see how enthusiasm for the Jets’ upcoming campaign is low.

Related: Jets May Not Get their RFAs Signed in Time

However, there are still plenty of reasons to be excited — hockey, after all, is the greatest sport in the world and captain Blake Wheeler has already promised the Jets are “going to have a bit of a chip on our shoulder” this fall (from ‘Wheeler already all-in for season’, Winnipeg Free Press, 08/23/19).

Blake Wheeler has promised the Jets will be raring to go come October, so start getting pumped up for the season, and for five games in particular. (AP Photo/Jeff Roberson). (Brad Rempel-USA TODAY Sports)

While all 82 games will be important, there are some that stand out in particular as must-see matchups. For your convenience, here’s a list breaking down just five you won’t want to miss.

Taking on Trouba in the Big Apple

Oct. 3, 2019 at New York Rangers

Season openers usually come with more hype than other games, but the hoopla surrounding this one should take the proverbial cake.

The Jets’ maiden 2019-20 contest will pit them against one of the most polarizing players to ever suit up for the franchise. Just four days after the Jets traded Jacob Trouba — whose lack of desire to play for the team that drafted him and never-ending contract saga became untenable distractions and made getting rid of him a necessity — to the New York Rangers, the schedule revealed the D-man would play his first-ever Blueshirts contest against the squad he spent six seasons with.

The #Rangers will have their season and home opener on Oct. 3 at Madison Square Garden against the Winnipeg Jets – meaning newcomer Jacob Trouba will get to face his old team in his first game as a Ranger https://t.co/PG8a3npMli via @ColinASteph pic.twitter.com/vhNsGVmeN7 — Newsday Sports (@NewsdaySports) June 25, 2019

One can’t possibly ask for a better storyline to kick things off. Trouba will be looking to make an impression in his new market, while the Jets will do their best to make his home debut one to forget.

Aside from seeing if the Jets start the season off on the right foot, this one’s worth watching just to see if Trouba’s former teammates target him and what he’ll do in response if they do.

Taking it Outdoors for the Heritage Classic

Oct. 26, 2019 vs. Calgary Flames

You’ll be able to catch the Jets outdoors for just the second time in franchise history as they and the Calgary Flames meet in the middle for the 2019 Tim Hortons NHL Heritage Classic at Regina’s beautiful Mosaic Stadium.

BREAKING: The @NHL has announced the 2019 @TimHortons NHL #HeritageClassic, where the #NHLJets will host the @NHLFlames at Mosaic Stadium in Regina, Saskatchewan on October 26, 2019! pic.twitter.com/5mQ4pOB8y6 — Winnipeg Jets (@NHLJets) January 1, 2019

Outdoor games are always a lot of fun and this matchup should be no exception. The author was lucky enough to attend the 2016 Heritage Classic in Winnipeg and has no doubt the 2019 edition will be a one-of-a-kind experience for all those in attendance from Regina, both teams’ fan bases, and elsewhere. It will come with plenty of pomp, circumstance, and extracurricular events.

Related: Jets and Flames’ 2019 Heritage Classic Storylines

It will also come with sparkling jerseys designed specifically for the occasion. The Jets knocked it out of the park by giving their WHA-era jersey a modern revamp and updated colour palette in 2016, and will reveal their 2019 Heritage duds later this month. Well-circulated concept art suggests the Jets will wear a blue 1990s-inspired uniform and the Flames will wear white.

To see players streak around in gorgeous retro-inspired duds — such as the Jets and Edmonton Oilers wore in 2016 — will be just one of many reasons to catch the 2019 Heritage Classic. (Bruce Fedyck-USA TODAY Sports)

The game will feature some of the NHL’s most exciting players, such as Mark Scheifele, Blake Wheeler, Johnny Gaudreau, and Sean Monahan (and young guns Kyle Connor, Patrik Laine, and Matthew Tkachuk, if they sign by then.) The Jets and Flames squared off three times last season, with the Flames coming out on top twice.

The Jets will be outdoors for the first time since 2016, while the Flames will be outdoors for the first time since 2011. (THE CANADIAN PRESS/Jeff McIntosh)

The potential the weather has to impact proceedings is yet another reason to tune in. There will be no sun delay (puck drop is 8 P.M. local time) but mother nature can bring just about any other conditions to the prairies on a late-October evening, including rain, wind, and even snow. Any adverse conditions could impact the way the game shakes out.

First-Round Rematch

Dec. 27, 2019 vs. St. Louis Blues

Jets and Blues fans will get a late Christmas gift in the form of a home-and-home series between Central Division rivals that begins with a Friday night matchup at Bell MTS Place.

It’ll be the first time the Jets and Blues tangle in 2019-20 and things should be raucous in the downtown rink — having the defending champion in your barn always ramps things up a bit.

It’ll also be the first time the teams tussle since the Blues knocked off the Jets in a nail-biting six-game series last April, which saw the road team win the first five games and all but one game decided by a single goal. The Jets should be chomping at the bit and ready exact a little revenge against the Blues for ending their season early.

Winnipeg Jets’ Kyle Connor celebrates with Mark Scheifele and Blake Wheeler after scoring the game-winning goal against the St. Louis Blues in Game 4 of last spring’s first-round series. (Jeff Curry-USA TODAY Sports)

The Jets went 3-1-0 against the Blues last regular season, but all the wins came prior to the Blues’ meteoric second-half rise. Those games included many great moments, such as a Jets’ third-period comeback and overtime victory and a five-goal game from Patrik Laine that capped off the Finn’s incredible November.

Trouba Returns to Town

Feb. 11, 2020 vs. New York Rangers

If the Jets are motivated to shut Trouba down and make his life miserable in his Rangers’ debut, they’ll be even more motivated to do so when he returns to the city he spurned for the first time.

This February evening will be Jets fans’ — who remember his 2016 holdout, his agent’s quarrelsome attitude, and his general derision for the place they call home — first chance to let Trouba know exactly what they think of him. Not many in Winnipeg buy the narrative that Trouba’s a selfless guy who left the city just so his fiancee could begin a medical residency.

Expect former-Jet Jacob Trouba to get a less-than-kind reception upon his return to Winnipeg in February. (Dennis Wierzbicki-USA TODAY Sports)

Expect plenty of boos, hostility, and perhaps even some creative signs and other efforts from those in attendance. Jets fans have been known to come up with novel ways to taunt those who’ve left the team on less-than-stellar terms, such as 2016’s tracksuit night upon then-Sabres’ Evander Kane’s return.

Jets Begin Divisional Drive Versus Wild

March 20, 2020 vs. Minnesota Wild

The always-competitive Central Division standings were in flux until the final days of last season. With most Central teams making huge additions this offseason (THW’s own Rob Mahon even called the division a “corridor of death”) expect things to come down to the wire again.

The Jets’ Central Division opponents have all stocked up. For example, the Colorado Avalanche snagged two-time 30 goal scorer and agitator extraordinaire Nazem Kadri. (THE CANADIAN PRESS/AP/Michael Dwyer)

Divisional games, as always, will be hugely important. The Jets controlled their own destiny last season but failed to snag the Central’s top spot due to their inability to beat divisional opponents late in the season, dropping three out of their last four.

The Jets probably won’t be in contention for the crown in 2019-20, but their final game of four versus the Minnesota Wild — the first of a stretch of four-straight against Central opponents through March 27 — will likely be of huge gravity and have a direct impact on whether they’ll be playoff-bound.

The Jets will need to find a way to best the Wild and other Central Division opponents in late March. (Photo by Jonathan Kozub/NHLI via Getty Images)

The Jets went winless against the Wild in five games last season and a couple of those defeats were among their most embarrassing and costly — a third period Black Friday meltdown in which they surrendered four-straight third-period goals stands out in particular.

They won’t be in any position to lose this one, though. You should be glued to your television for this game; maybe book the whole week off work just to be safe.

Which game(s) are you the most pumped for? Are there games on your “must-see” list that did not make it onto ours? Comment below!