Four NHL Legends Chasing History This Season—And How to Bet on It

Alexander Ovechkin just became the first player in NHL history to score 900 goals. Let that sit for a second. On November 5th against St. Louis, the 40-year-old snapped a backhand past Jordan Binnington, cleared the bench, and cemented himself as the league’s most relentless goal-scorer ever. He passed Gretzky with No. 895 last April. Now, in a potential farewell season, he’s still pushing for historic marks — and motivation’s not in question.

But Ovi isn’t the only legend writing history this season.

While the NHL world watches the Great 8 potentially hang up the skates after one last run, four other future Hall of Famers are quietly closing in on career-defining numbers. We’re talking 500 goals, 600 goals, 1,300 points, and a torch-passing moment in Pittsburgh that might make you feel something.

Below, we break down four massive NHL milestones on the horizon—when they’ll likely happen, what they mean, and how you can bet into the moments when history’s about to be made.

1. Steven Stamkos – 600 Career Goals

The Milestone: Only 21 players in NHL history have scored 600 goals. Stamkos needs 15 more to join them—putting him in the same conversation as Jari Kurri, Bobby Hull, and Dino Ciccarelli. Not bad for a guy who’s spent the last decade quietly being one of the league’s most lethal pure finishers.

Where He Stands: Stamkos is at 585 goals through 1,181 games. The problem? He’s got just 3 goals in 17 games this season with Nashville. The power play production that defined his Tampa years has dried up—Nashville’s PP unit ranks well below league average, and Stamkos isn’t getting the same touches he once did. But there’s a pulse: he scored a PPG against Dallas in early November, his first sign of shaking off the early-season rust.

Timeline Projection: At his current pace, Stamkos should hit 600 somewhere around mid-to-late December. I’ve got my eye on December 20th vs. Toronto — a prime-time matchup with plenty of spotlight. If he heats up, it could come earlier. If the slump drags, it might slip into the new year.

Betting Angle: Target anytime goal scorer props in home games, especially as he approaches 598 or 599. The narrative spots matter here—games like Toronto (Dec 20) or the post-holiday stretch could see teammates actively feeding him. Nashville’s offense needs a spark, and a Stamkos milestone could be the feel-good storyline they rally around.

2. Patrick Kane – 500 Career Goals

The Milestone: Kane sits at 494 goals, just six away from becoming the 50th player in NHL history to hit 500. For a guy who built his legacy on clutch moments and silky mitts, this one feels inevitable—but the timeline’s tighter than you’d think.

Where He Stands: He started the season hot—2 goals and 3 assists in six games—before missing nine games with an upper-body injury in October. He returned on November 7th against the Rangers, and Detroit’s pushing for its first playoff spot in a decade. At 36 (turning 37 on November 19th), Kane’s also eyeing a 2026 Olympic roster spot, so health and production matter more than ever.

Timeline Projection: If Kane stays healthy and maintains his early pace, 500 could come before Thanksgiving. Best-case scenario? He hits it right around his birthday on November 19th, in front of a home crowd. Detroit faces Seattle on the 18th and the Islanders on the 20th. More realistically, look for it in late November or early December — especially if the Red Wings lean into the narrative and start feeding him once he’s sitting on 498 or 499.

Betting Angle: Watch anytime goal scorer props closely once he hits 498. Home games against weaker defensive teams are your spots—Detroit will absolutely try to get him the puck in milestone territory. The DeBrincat connection matters here: these two have chemistry, and when Kane gets hot, he scores in bunches. Books may overprice him as the milestone is one away, so look to hammer the prop when he is 2 away. Kane can still have multi-goal nights on a good day.

3. Sidney Crosby – 1,723 Career Points (Passing Mario Lemieux)

The Milestone: Crosby needs 18 more points to pass Mario Lemieux for 8th all-time in NHL scoring. This isn’t just a number—it’s a crown inheritance. Lemieux was more than Crosby’s mentor — he drafted him, took him in, and literally gave him a room in his house. Now, twenty years later, Crosby’s about to pass him in the same sweater, for the same franchise. That’s the kind of poetic symmetry you couldn’t script if you tried.

Where He Stands: Crosby sits at 1,707 points (636 G, 1,071 A) through 1,368 games. He’s playing like age is a suggestion—20 points in 16 games this season, leading the Penguins in both goals and scoring while tied for the NHL lead in goals at the time of this article. Pittsburgh’s power play is humming at 36% efficiency, giving Crosby setup opportunities on a nightly basis.

Timeline Projection: At 1.25 points per game, Crosby should pass Lemieux around Game 30—December 13th vs San Jose. Mark it down. Once he’s within 2–3 points, expect his teammates to feed him every chance they get. They know how much this milestone means — and they’ll want their names on the scoresheet with him.

Betting Angle: Target 2+ points props and assist props in the games leading up to December 13th, especially home games. Crosby in milestone territory with a hot power play is a betting goldmine. “To record a point” parlays paired with Penguins wins also carry value here—Pittsburgh will rally around this moment.

4. Anze Kopitar – 1,300 Career Points

The Milestone: Kopitar needs 15 more points to hit 1,300—a mark that would tie him with Jarome Iginla and push him toward legends like Pierre Turgeon, Mike Gartner, and Denis Savard.

Where He Stands: The Kings captain sits at 1,285 points (441 G, 844 A) through 1,465 games. He’s playing 0.64 points per game this season—7 points in 11 games, leaning heavily on his playmaking with 6 assists and just 1 goal. At 37, Kopitar’s clearly in the distributor phase of his career, but he’s still quarterbacking LA’s offense and logging meaningful minutes. A two-time Stanley Cup champion and Selke winner, he’s spent his entire 20-year career in LA and will likely retire as the franchise’s all-time points leader once he pads the cushion.

Timeline Projection: At his current pace, Kopitar should hit 1,300 around Game 34—December 18th vs Tampa Bay. If he heats up or the Kings start clicking offensively, it could come a few games earlier. Circle the December 13th-31st schedule window—that’s your milestone zone.

Betting Angle: Assist props are your best bet here. Kopitar’s not hunting goals—he’s setting the table. Target 2+ points props against weaker defensive teams during the December stretch. There’s also real narrative juice here: with retirement on the horizon, teammates will absolutely try to feed the captain for his milestone, especially in home games. Look for plus-money value on his assist and multi-point props as he approaches 1,298 or 1,299—books may underprice the “help the legend” factor.

Four Hall of Famers Still Getting It Done

This season isn’t just about playoff races and division titles — it’s about legacy. Stamkos is joining the 600-goal club. Kane is hitting 500. Crosby is passing the man who gave him a place to live — and a franchise to lead. Kopitar is quietly cementing his place among the all-time greats, still wearing the only sweater he’s ever known.

It’s rare to have this much history stacking up at once. And the thing about milestones? They don’t wait. These windows are tight, the timelines are real, and the betting opportunities are sitting right there in December and early 2026.

Ovechkin reminded us what chasing immortality looks like. Now it’s their turn.