The National Hockey League (NHL) has a total of four games on tap for Monday night, including the Pittsburgh Penguins and Toronto Maple Leafs tangling at 7:30 p.m. ET on NHL Network.
We'll provide single plays and parlay opportunities you could potentially pair with the Week 9 NFL Monday Night Football game, NBA action, and, for the first time this season, NCAA basketball games. Good luck with all of your plays! Let's get started.
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NHL Monday Picks & Parlay Tips: Expert Odds, Predictions & Best Bets Tonight
For the latest NHL Odds, including NHL Futures and NHL player props, visit RotoWire's NHL Betting page. For up-to-date NHL player news and NHL Injury Report info, head to RotoWire's NHL Lineups page. You can find more picks at Bookies.com/picks. Here are our NHL Best Bets today, featuring expert NHL picks for an action-packed slate of games.
NHL Monday Night: Top Betting Picks and Parlay Insights
Pittsburgh Penguins 
at Toronto Maple Leafs 
The Penguins (8-3-2) and Maple Leafs (6-5-1) square off at 7:30 p.m. ET at Scotiabank Arena in Toronto, and that game can be viewed or streamed on NHL Network.
Last season, Toronto won the season series 2-1, with the home team also going 2-1. The Leafs have won four of the past five matchups in the series, outscoring the Pens 22-14, with the Over holding a slight 3-2 advantage in the span. In the past nine meetings, the underdog has a 5-4 advantage as well.
Pittsburgh wraps up a four-game road trip. It is 1-1-1 in the first three games, and it comes off a 5-2 loss in Winnipeg on Saturday, losing to backup goaltender Eric Comrie. It was the first loss in regulation in nine games, as the Penguins have picked up 14 out of a possible 18 points since Oct. 16. The Over is 7-3-2 in the previous 12 games, too.
Tristan Jarry (5-1-0, 2.35 GAA, .923 SV%, 1 SO) is expected to get the starting nod for Pittsburgh in this one, with Anthony Stolarz (4-4-1, 3.13 GAA, .893 SV%) likely for the Leafs. The goaltending scales are tipped in favor of the visiting Penguins, and that's the way we'll go with our play.
With the Over run for the Penguins lately and a seven-game Over streak for the Maple Leafs, we'll certainly be going high on the total.
- Penguins ML (+150 at ESPN Bet and FanDuel Sportsbooks)
- Over 6.5 Goals (-105 at BetMGM, Caesars, DraftKings, ESPN Bet Sportsbooks)
Don't make any bets on your favorite sports betting apps without first consulting the latest NHL odds.
Edmonton Oilers 
at St. Louis Blues 
The Oilers (6-4-3) and the Blues (3-7-2) meet at Enterprise Center in St. Louis, with a puck drop set for 8:30 p.m. ET on ESPN+.
Edmonton swept the regular-season series in 2024-25, winning each of the three meetings, although two of the wins were in one-goal games. The Under cashed in two of those games, including a 3-2 overtime win on Feb. 4 as heavy favorites (-185) as the total went low.
Edmonton has had a flare for the dramatic lately, going to overtime in three of the past four games. It is 2-0-2 across the past four matchups, with the Over cashing in three of those contests.
Stuart Skinner (4-3-2, 2.51 GAA, .900 SV%, 1 SO) has been playing well for the Oilers, and he is expected to be opposed by Jordan Binnington (2-4-2, 3.21 GAA, .860 SV%).
The Blues are skidding hard, going 0-5-2 in the past seven games, last tasting victory Oct. 18. While the Under cashed in Saturday's 3-2 loss at Columbus, the Over is 5-1 in the past six games.
We'll definitely be playing the Over in this battle, and based on Edmonton's season sweep, as well as the nosedive of St. Louis lately, we'll back the moderate favorite Oilers.
- Oilers ML (-140 at Bet365, BetMGM, Caesars, DraftKings and Fanatics Sportsbooks)
- Over 6 Goals (-115 at BetRivers Sportsbook)
Chicago Blackhawks 
at Seattle Kraken 
Casual hockey fans might not know this, but both the Blackhawks (5-4-3) and Kraken (5-2-4) have winning records through the first month of the season. They meet each other at 10:00 p.m. ET at Climate Pledge Arena in Seattle on ESPN+.
The Kraken have won four of the past five meetings in this series, and Seattle has won five in a row at home against Chicago. In fact, the Blackhawks won their first-ever trip to Climate Pledge Arena on Nov. 17, 2021, and they haven't won in Seattle since. The Kraken have outscored the Blackhawks 26-9 in the five-game home winning streak, with the Over holding a slight 3-2 edge in those games.
However, Chicago is playing well this season, bringing it every night. It is 5-2-2 in the past nine outings, coming off a 3-2 overtime loss in Edmonton on Saturday. The Under has a 5-2 edge in the past seven games.
Seattle enters with back-to-back overtime losses against Original Six teams -- the Canadiens and the Rangers. Over the past 10 games, the Kraken has gone to overtime or a shootout six times, going 2-0-4 in those matchups. The Under is also 4-1 in the past five games.
For the total, we're going low for sure. For the line, we'll take the Blackhawks catching the goal and a half, looking for overtime or a shootout.
- Blackhawks +1.5 Goals (-185 at BetMGM)
- Under 6 Goals (-118 at BetMGM)
Value NHL Parlays for Monday Night Games
6-Leg NHL Super Parlay (+3932 at FanDuel Sportsbook)
- Penguins ML and Over 6.5 SGP (+332)
- Oilers ML and Over 6.5 SGP (+226)
- Blackhawks +1.5 and Under 5.5 SGP (+114)
3-Leg NHL Totals Parlay (+733 at FanDuel Sportsbook)
- Over 6.5 (-110) - Penguins at Maple Leafs
- Over 6.5 (+104) - Oilers at Blues
- Over 6.5 (+114) - Blackhawks at Kraken
2-Leg NHL Best Same-Game Parlay (+332 at FanDuel Sportsbook)
- Penguins ML (+150) and Over 6.5 (-110)
