Simply having the best player in any given league is hardly a guarantee that championships will follow. If that was the case then we would have watched Sidney Crosby and Alex Ovechkin trade Stanley Cups for the past 10 seasons.

The Memorial Cup is no different. While many of the game’s top prospects absolutely tore up the junior ranks ahead of their respective draft days, individual teenage dominance doesn’t always equal team success.

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Connor McDavid is a generational talent. By the numbers, he’s outperformed Crosby’s draft-year run. He may have a shot at besting Crosby’s shot at Memorial Cup glory, too, as McDavid’s Erie Otters are set to take on the Oshawa Generals in the Ontario Hockey League championship.

Here’s a look at how some of the top prospects of all-time have fared in their quest for junior hockey’s top prize.

Bobby Orr

Orr led the Oshawa Generals to the 1966 Memorial Cup, when the trophy was still open to all junior A teams in the country. Orr’s Generals fell short in a best-of-seven final, losing to the Edmonton Oil Kings of the Central Alberta Hockey League in six games.

In a tournament format much different than that of today, Orr had 12 goals and 36 points in 12 games.

Guy Lafleur

Lafleur compiled 379 points in 118 games with the Quebec Remparts of the QMJHL. He had two shots at the Memorial Cup.

The Remparts lost in the semi-final in 1970, but Lafleur would guide the club to glory in 1971 with a win over the Oil Kings in a best-of-three series. Lafleur scored nine goals and 14 points in seven games during the Remparts’ run to the title.

Wayne Gretzky

A list of Gretzky’s achievements could fill an IMAX screen. One piece of hardware the Great One never put his hands on is the Memorial Cup. He never even had a shot.

Gretzky finished second to Bobby Smith for the OMJHL scoring title in 1977-78, and his Sault Ste. Marie Greyhounds would bow out of the 1978 playoffs after falling to Smith’s Ottawa 67’s in the quarter finals.

Mario Lemieux

Lemieux finished the 1983-84 QMJHL season with 133 goals and 282 points. He guided the Laval Voisins to the 1984 Memorial Cup tournament, but they would finish 0-3 while Lemieux recorded a pedestrian one goal and two assists in three games.

Eric Lindros

“The Big E” was a man among boys for the better part of his junior career with the Oshawa Generals.

The first overall pick in the 1991 NHL Entry Draft led the Generals to the 1990 Memorial Cup, which was capped by a dramatic 4-3 double-overtime win versus Kitchener Rangers in the final. Lindros was named a tournament all-star and finished with nine assists in four games.

Alexandre Daigle

Daigle was supposed to be “the next one.” Instead, he stands as one of the greatest NHL draft busts of all-time.

Before the Ottawa Senators took him first overall in 1993, Daigle totalled 45 goals and 137 points in 53 games with the Victoriaville Tigres in the 1992-93 season. His Tigres fell to the Drummondville Voltigeurs in six games in the quarter finals of the QMJHL playoffs.

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Sidney Crosby

With 66 goals and 168 points in 62 games with the Rimouski Oceanic, not to mention a gold medal at the 2005 IIHF World Junior Championship, Crosby’s draft-year run was rather legendary by today’s standards.

The magic ran out for the Oceanic in the 2005 Memorial Cup when they lost to Crosby’s Team Canada teammate Corey Perry and the London Knights in the final. No. 87 recorded six goals and 11 points in five games.

Steven Stamkos

Stamkos scored 58 goals in 61 games in his final season with the OHL’s Sarnia Sting. His ability to lead the club to junior hockey’s holy grail was extinguished by the Kitchener Rangers in a sweep of the 2008 OHL conference semifinals.

John Tavares

Tavares entered his draft year with a ton of hype, which he appears to have delivered on through the first six years of his NHL career.

Tavares couldn’t reach the Memorial Cup with the Oshawa Generals, and not even a move to the London Knights in his final junior season could help him get there. The Knights lost to eventual 2009 Memorial Cup champions the Windsor Spitfires in the OHL’s conference finals.

Taylor Hall

Taylor or Tyler? That was the debate that raged on through Taylor Hall and Tyler Seguin’s draft year.

While it’s the latter who holds a leg up in their pro careers thus far, it’s the former who found more success in the OHL. Hall, who was selected first overall by the Edmonton Oilers in 2010, won two Memorial Cups with the Windsor Spitfires (2009 and 2010).