The first weekend of NHL betting is upon us, my degenerate friends, with a juicy 13-game slate on tap for the premier Saturday of the 2026-27 season. Before we get too hot-and-heavy into our top-3 selections and favourite side bets for today’s board, we have to throw out the disclaimer that the first week or two of NHL wagering is perennially a dicey stretch of the schedule to tear up. However, there are still a number of angles to sprinkle on, so let’s tap in and get this paper.

Final 2025-26 Saturday Record (Daily Record Tracked/Posted @Flips_Picks):

Gold: 8-9
Silver: 10-7
Bronze: 13-4
Side Bets: 22-27

GOLD SELECTION — Cole Caufield Anytime Goal (+155)

The Montreal Canadiens are one of the most exciting young teams in the NHL, and they head into Pittsburgh having gone 2-1 against the Penguins last season. But the spot we want to target here is Mr. Saturday Night himself, Cole Caufield. The young American was absolutely lights out on Saturdays last season, racking up 21 goals and 14 assists in 23 Saturday games for a ridiculous 35 points overall. That’s not some tiny-sample-size trend either — we’re talking about 23 games worth of evidence that Caufield really did find another gear on hockey’s biggest night.

Now, we’re obviously dealing with a brand-new season, so we wouldn’t go overboard treating that Saturday split like some sort of mystical betting formula. But when we combine it with the matchup, we absolutely want a piece.

Pittsburgh is entering the season with some questions in goal, with Arturs Silovs and Sergei Murashov expected to carry Crosby and the boys back to the postseason. In addition, the Penguins also have some injury concerns heading into this one with Ben Kindel, Bryan Rust, and Blake Lizotte all shelved. Montreal, meanwhile, already opened the season with a 3-2 win over Toronto and should have plenty of confidence heading into Pittsburgh.

Caufield has seven points in 14 career regular-season games against the Penguins, including three goals, and this is exactly the type of matchup where we want to back his finishing ability.

Saturday Caufield? Yeah, we’re buying it.

SILVER PICK — Auston Matthews Anytime Goal (+155)

Auston Matthews at home against the Ottawa Senators is a situational dream spot for an anytime-goal bet. Matthews absolutely owns this matchup historically, registering 52 points in 37 career regular-season games against Ottawa. That’s a ridiculous 1.41 points per game, with Matthews finding the back of the net in 26 of those contests.

And while the Senators have had Toronto’s number at various points recently, that’s actually part of what makes this matchup interesting for us. Ottawa is coming into Toronto for its season opener, while the Leafs already have two games under their belt after opening the season against Montreal in losing fashion and following that up with a neat-and-tidy dub against the New York Islanders. This isn’t a game where we’re necessarily looking to hammer the Maple Leafs on the moneyline. Instead, we’re isolating the guy who has consistently made life miserable for this particular opponent.

Matthews hasn’t scored yet this season, and we’re not interested in overreacting to two games with so many new faces in the lineup — but if you’re looking for a bounce-back goal spot for one of the best pure finishers on the planet, this is it. The volume, the history, and the matchup all point in the same direction.

BRONZE PICK — Macklin Celebrini Anytime Assist (-165)

A triple-threat of player prop bets to open the year? WHY NOT!

Macklin Celebrini is quickly becoming a nightly cheat code for prop bettors, and he opened the season with a trifecta of assists in a wild 4-3 overtime win against the Florida Panthers on Thursday. The third-year superstar was involved in all three San Jose goals, including assists on both of Will Smith‘s goals before helping set up Luca Cagnoni‘s overtime winner. He also fired seven shots on goal. That’s the type of all-around involvement we’re looking for when attacking an assist prop.

Celebrini isn’t simply a one-dimensional goal scorer. He’s the engine that drives basically every dangerous Sharks offensive sequence, and his ability to contribute on the power play, at even strength, and even shorthanded gives him more ways to land a prop than your traditional offensive superstar.

And then there’s the opponent.

San Jose scored 11 goals across three meetings with Los Angeles last season, winning two of those games, while the Kings allowed 3.67 goals per game against the Sharks in that season series. Celebrini finished his second NHL season with 45 goals and 115 points across 82 games, and now he’s coming off a three-assist performance to open his third campaign.

We’re not asking him to repeat the hat trick of helpers. Give us one apple and let’s cash it.

Side Bets

Ottawa Senators @ Toronto Maple Leafs – Pick: Over 5.5
Montreal Canadiens @ Pittsburgh Penguins – Pick: Canadiens ML
Boston Bruins @ Minnesota Wild – Pick: Quinn Hughes Anytime Assist

Flip Livingstone is an NHL betting expert, fantasy writer, and daily podcast host with the Locked On Fantasy Hockey pod. He also has experience at outlets such as theScore NHL, Postmedia, and Hockey Night in Canada. You can follow him @Flips_Picks.