As fans of both the NFL and the CFL know, the Lombardi Trophy and the Grey Cup are among the most coveted prizes in professional football. Winning either one is an incredible achievement and both tournaments can create electric atmospheres among their viewers – but to lift both cups is a rare feat that only a select few players can boast about. Naturally the former is the one that the players crave more than anything, but the latter is also a highlight in one’s career, and both leagues have the postseason on their minds.

For Canada, the playoffs there have just wound down. The Winnipeg Blue Bombers appeared in their fourth straight Grey Cup back on November 19th, but for the second consecutive campaign they were defeated. Last year it was the Toronto Argonauts who picked up a razor-thin one-point victory and this year it was the Montreal Alouettes, winning 28-24 at Tim Hortons Field in Hamilton. The triumph was the Quebec side’s first in 13 years and now the CFL odds for this year have made them the +500 second favourites for glory once more.

Over in the NFL meanwhile, they are just about to get underway and it is the San Francisco 49ers who are the +180 favourites to triumph over the rest. They are the top seed in the NFC and have proven themselves to be the team to beat, especially considering the fact that heavyweights such as the Kansas City Chiefs and the Philadelphia Eagles have both been in free fall in recent weeks. They are expected to meet the Baltimore Ravens at Super Bowl LVIII at Allegiant Stadium in Las Vegas next month, who are the top seeds in the AFC and the +330 second favourites for the Lombardi.

But do you know what’s better than winning a Super Bowl or a Grey Cup? Winning them both, of course! Over the years, several legendary players have achieved this incredible feat, proving their exceptional skills on both sides of the border. Let’s take a look at some of the most high-profile names on the list.

Warren Moon

This Canadian-born quarterback had an illustrious career in both leagues, earning spots in nine Pro Bowls and winning five Grey Cups before eventually joining the NFL’s Houston Oilers. He would go on to make nine more Pro Bowls, leading the league in passing yards twice and taking the Oilers to the AFC Championship game in 1992 and 1993. Moon’s crowning achievement, however, came in 1999 when he won Super Bowl XXXIV with the Seattle Seahawks.

Joe Kapp

A true dual-threat QB, Kapp spent the majority of his career in the CFL, winning two Grey Cups with the BC Lions before jumping to the NFL’s Minnesota Vikings in 1967. He would lead the team to a 12-2 record and a spot in the Super Bowl, where they would lose to the Chiefs in Super Bowl IV. Kapp’s fiery personality and passionate style of play made him a beloved figure in both leagues and a favourite among fans.

Doug Flutie

Arguably one of the most famous CFL players of all time, Flutie’s success in the league (three Grey Cup championships and two CFL Most Outstanding Player awards) paved the way for his eventual return to the NFL. After a few tumultuous years with the Chicago Bears and New England Patriots, Flutie landed with the Buffalo Bills in 1998 and led them to the playoffs in his first season. Although he never won a Super Bowl, Flutie’s legacy endures as a quarterback who could succeed in any league.

Tom Clements

Clements is a bit of an outlier on this list, as he only won one Grey Cup (with the Ottawa Rough Riders in 1976) and never started more than two games in an NFL season. However, his contributions to the league as a player and coach cannot be denied. Clements spent over a decade coaching in the NFL, including stints as the offensive coordinator for the Green Bay Packers and Buffalo Bills.

Rocket Ismail

The only player on this list to win a Grey Cup after already winning a Super Bowl, Ismail’s journey to football glory is a fascinating one. After winning a national championship with Notre Dame in 1988, Ismail spent two seasons in the CFL with the Toronto Argonauts before being drafted by the Los Angeles Raiders. He would go on to win Super Bowl XXVII with the Dallas Cowboys in 1993 before returning to the CFL and winning two more Grey Cups with the Argonauts.

Hank Ilesic

Moving on, we have Hank Ilesic, a punter who is widely regarded as one of the best in CFL history. Ilesic won three Grey Cups during his career with various teams before being recruited by the Dallas Cowboys. In 1993, he helped the Cowboys win Super Bowl XXVIII, making him one of the few players to ever win both the Grey Cup and the Lombardi Trophy as a punter.