The NHL season produces milestone moments almost every night, but knowing which ones are actually worth paying attention to requires more than checking the record book.
That's where the NHL Milestone Tracker comes in.
Each day, I'm scanning the schedule for players closing in on meaningful career marks, franchise records, birthdays, and other notable spots before digging into the matchup.
Sidney Crosby gives the tracker a fitting launch point. The Penguins captain enters tonight tied with Joe Thornton for seventh on the NHL’s all-time assists list, leaving him one helper away from moving into sole possession of the spot.
Crosby’s chase for history also gives us one of the more interesting angles among NHL picks for Monday, Oct. 4.
NHL Milestone Tracker top picks
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Crosby Over 0.5 assists Percentages courtesy of Novig, one of the best prediction market apps.
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Jets vs Penguins: Crosby chases assist milestone
Sidney Crosby enters tonight one assist away from taking sole possession of seventh place on the NHL's all-time assists list.
The milestone is what got him onto the tracker, but the matchup is why I'm interested in the assist market.
Crosby has picked up an assist in each of Pittsburgh's first two games, and the Pittsburgh Penguins have come out flying offensively with 13 goals already. He's still running the show at even strength and on the power play, so the opportunities should be there again tonight.
The Winnipeg Jets aren't exactly walking into this one fresh, either. They're on the second half of a back-to-back and playing their third game in four nights, while Pittsburgh has played just twice through the first six days of the season.
So yes, the history is the hook. But I'm not taking Crosby just because he's chasing a record. Pittsburgh is scoring, Crosby is already creating, and Winnipeg is in a rough schedule spot. That's enough for me to back Over 0.5 assists.
Other NHL milestones to watch
Nino Niederreiter chasing point No. 500
Tracker status: Repeat
Nino Niederreiter is still sitting on 499 career points, making this the third straight game he's entered one away from No. 500.
There's no point market available for Niederreiter tonight, so the only way to attack the milestone on Novig is through his anytime goal market, which is trading at a 16% probability.
That's firmly in long-shot territory, and his early-season usage doesn't exactly scream must-play. Niederreiter is skating on Winnipeg's fourth line, has been held without a point through three games, and is averaging just 11:46 of ice time.
This isn't one I'd force, but if you're looking for a milestone long shot tonight, Niederreiter is the one.
NHL milestones on the horizon
Kyle Connor — 3 games from 700 career games
Kyle Connor is quickly closing in on another round number. After playing Sunday against Detroit, the Jets winger sits at 697 career games, which means baring injury, game No. 700 comes at home vs. the Anaheim Ducks on Friday night.
Mikael Granlund — 1 goal from 200
Mikael Granlund moved to 199 career goals with his overtime winner against Florida and will enter Anaheim's next game one away from No. 200. The Ducks take on the Edmonton Oilers on Wednesday, October 7.
Recently reached NHL milestones
Cole Perfetti — 100 career assists
Cole Perfetti came into Sunday sitting on 98 career assists and needed just one night to wipe the milestone off the watchlist. He recorded two helpers against Detroit, with his assist on Kyle Connor's second goal officially giving him No. 100 for his career.
Dylan Strome — 600 career games
Dylan Strome reached 600 career NHL games Saturday when Washington visited Tampa Bay. The Capitals center has been remarkably durable since arriving in D.C., appearing in 326 of Washington's first 329 games since signing with the club in 2022.
Gabriel Landeskog — 800 career games
Gabriel Landeskog officially reached 800 career games in Colorado's 6-1 win over St. Louis on Saturday. He became just the sixth player in franchise history to reach the mark and celebrated by adding an assist on Martin Necas' second goal of the night.
Andrei Vasilevskiy — 600 career games
Andrei Vasilevskiy made career game No. 600 count, stopping 19 shots in Tampa Bay's 3-1 win over Washington. The victory was No. 371 for Vasilevskiy, the most by any goaltender through his first 600 NHL games.
How the NHL Milestone Tracker works
The NHL Milestone Tracker is designed to identify noteworthy player and team situations before the milestone becomes the story.
The tracker monitors career totals across goals, assists, points, and games played while also accounting for birthdays, notable events, and potential franchise records throughout the NHL season.
Each daily scan then separates those situations into different stages.
New indicates a player has entered the relevant milestone range for the first time. Repeat means the player remained within range after a previous game, while Stale helps identify milestones that have lingered long enough that they may no longer deserve the same level of attention.
Those triggers are only the starting point.
Once a player is flagged, we evaluate the matchup, recent production, role, schedule, opponent, and available prediction markets to determine whether the milestone creates something worth highlighting.
Some milestone chases will produce an actionable market. Others will simply be worth monitoring until the situation changes.
The goal is simple: identify what's coming before the moment arrives, then determine whether the numbers surrounding it deserve our attention.
Odds are correct at the time of publishing and are subject to change.
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