Seven of those matchups, came during the Conference Semi-finals, where the Ovie-Sidney rivalry escalated to new heights.
Tonight, the rivalry continues.
The Pittsburgh Penguins and Washington Capitals will skate together for the first time since the Penguins eliminated the Caps in a Game Seven, 6-2 blowout, en route to their Stanley Cup victory last season.
Both Crosby and Ovechkin play at such an elevated level to begin with, but when they face each other, a whole new element of intensity is introduced.
"To say that we absolutely hate each other, I don't think so, but we're competitive guys, and that's the result of everything and the way it's kind of built up," said Crosby during an interview with ESPN's Pierre LeBrun.
"I don't think there's any lack of respect there at all. We're just different in a lot of ways."
That difference between the two is what makes these two superstars even more amazing to watch.
Crosby, the poster boy of the NHL, is without a doubt the more finesse. His vision is top-notch and can put the puck in places that very few can. He's also doing something else this season that he normally doesn't: Scoring goals.
Through 50 games this season, Crosby has scored 32 goals going into tonight's matchup.
Don't get me wrong, Crosby is also a talented goal scorer, but his puck possession and playmaking skills is where he is in a world of his own. The Kid, who's previous high in goals, 39, is on pace to shatter that mark by season's end.
Ovechkin, on the other hand, is the definition of a hockey player.
He's tough, he's mean, he's an animal. All that while being arguably the most prolific goal scorer the NHL has ever seen. He's got a North American mentality in a Russian's body—a lethal combination to say the least.
Ovechkin can dangle with the best of them and fake defensmen out of their skates. Or he'll simply just blast the puck by you, and your goalie. His shot is simply explosive. The fact that he has led the NHL in shots since he's been in the league doesn't bode well for goalies.
Or, if plans A and B don't pan out, Ovechkin comes with plan C, where he will simply just skate right through you.
In no way, shape, or form, does Ovechkin shy away from contact, most of the times he's initiating it—an area that Crosby tends to stay away from.
"Off the ice, I can shake hands and say hi like normal people, but on the ice, you don't have friends," said Ovechkin to LeBrun. "But right now on the ice, he's [Crosby] my rival, just like everybody."
Another area that Ovechkin separates himself from Crosby in, is showmanship.
Crosby prefers the low-key, quiet humble approach. Where as Ovechkin, knows such words. He's got a personality and a fire that he exemplifies on every shift. He's the NHL's equivalent to Chad Ochocinco when it comes to celebrations.
Besides being a deadly goal scorer, he's got an entertainment value to him that the NHL desperately needs.
Since they both made their debuts in 2005, their stat lines have been very similar when playing each other during the regular season.
Ovechkin: 12 GP, 7 G, 8 A, 81 SOG, 23:18 ATOI.
Crosby: 11 GP, 5 G, 12 A, 41 SOG, 21:33 ATOI.
Besides the Winter Classic, if there is one regular-season matchup that will get outsiders to watch the NHL, this is it.
Except tonight, unfortunately.
I don't know what God the NHL schedule maker prays to at night, but he surely must have had a sin-full year before he made the 2009-10 NHL schedule.
Unfortunately for the NHL, Ovechkin-Crosby lands on the same night as LeBron-Kobe.
For us rabid NHL fans, there is no question which superstar showdown we are going to watch, but to the average sports fan, LeBron and Kobe will, literally and figuratively, steal the show.
Not to mention that the only way you could see the Caps-Pens game is on the NHL Network, while the Lakers-Cavs have primetime on TNT.
But, for those of us who will be watching tonight, there is no question in my mind that Ovechkin and Crosby wont steal our show.