Possibly the most memorable games between the Toronto Maple Leafs and Carolina Hurricanes came during the 2002 Stanley Cup Eastern Conference Final when the Canes came in as underdogs only to beat the Leafs in six games.

While the recent transactions between these two clubs don’t exactly live up to the hype that was the six-game series back in 2002, there have been some names swapped between the Canes and Leafs over the years.

With that said, here’s a look at the five most recent deals between the two clubs.

Swapping Defence

The most recent transaction happened back on Jan. 1, 2014. The Leafs moved veteran defenceman John-Michael Liles and defensive prospect Dennis Robertson to the Hurricanes for another veteran defenceman in Tim Gleason.

Related: Maple Leafs’ Recent Dealings With the Flames

While Robertson hasn’t cracked the NHL roster yet, still reserving a spot on the AHL’s Charlotte Checkers, Liles spent parts of three seasons with Hurricanes following the trade. During that time, Liles tallied 10 goals and 46 points in 156 regular season games before heading to Boston where he last played in 2016-17.

Gleason finished the year with the Leafs before re-joining the Hurricanes. (Amy Irvin / The Hockey Writers)

Going the other way, Gleason played just 39 games with the Leafs finishing off the 2013-14 season. Over that span he recorded five points. Following the end of the season, he signed back with the Hurricanes and was traded to Capitals later in the year where he finished his NHL career.

Giving Up Tlusty

Before the Gleason deal, the Leafs and Hurricanes hadn’t engaged in a trade since Dec. 3, 2009. While it was more of a minor deal at the time, the Canes would end up with a player that would spend a fair amount of time within their organization.

The Leafs acquired the rights to Philippe Paradis in exchange for Jiri Tlusty. Paradis signed a three-year entry-level deal with the Leafs in Apr. 2010 and he was quickly moved to the Chicago Blackhawks two months later. He never played for the Leafs and never had any luck cracking an NHL roster.

Tlusty became a mainstay in the Hurricanes’ roster following the trade. (Photo By Andy Martin Jr)

As for Tlusty, he played 322 regular season games for the Hurricanes over parts of six seasons. He scored 76 goals and 145 points before being traded to the Jets in 2014-15. He played 30 games for the Devils in 2015-16, but hasn’t played in the NHL since.

Acquiring O-Dog

On Jul. 30, 2005, the Leafs might’ve made one of their biggest acquisitions from the Hurricanes’ organization. The Leafs acquired veteran forward Jeff O’Neill in exchange for a conditional fourth-round pick in the 2006 NHL Entry Draft.

The Canes moved the pick to the St. Louis Blues in a deal that got them Doug Weight, while the Blues eventually used it to draft goaltender Reto Berra with the 106th overall pick.

O’Neill spent two seasons with the Leafs before he retired following the 2006-07 season. Through 148 regular season games with Toronto, he tallied 39 goals and 80 points – falling one goal shy of two 20-goal seasons.

The Legend, Ron Francis

Before O’Neill, it was Francis – the Hall-of-Fame forward the Leafs acquired from the Hurricanes on Mar. 9, 2004. In return, the Leafs sent Carolina a fourth-round pick in the 2005 Entry Draft.

The Hurricanes used the pick in another trade on Jul. 30, 2005, with the Columbus Blue Jackets with the Jackets using it to draft Jared Boll 101st overall.

Ron Francis had 10 points in 12 games with the Leafs following the trade. (Photo by Dave Sandford/NHLI via Getty Images)

As for Francis, he played just 12 games for the Maple Leafs to finish the 2003-04 season and his career. What might’ve been most impressive is that he tallied 3 goals and 10 points in those 12 games. He added four assists in 12 postseason games with the Leafs, but eventually returned to the Hurricanes as their general manager – a post he holds today.

A Druken State of Mind

No, this heading isn’t spelt wrong. In fact, it has to do with the fifth most recent trade between the Leafs and Hurricanes that took place on May 29, 2003. In the deal, the Leafs acquired centre Harold Druken for defenceman Allan Rourke.

Related: Maple Leafs’ Recent Business With the Bruins

Druken played just 14 games for the Leafs over parts of two seasons collecting six assists over that span. Rourke, on the other hand, played 25 games for the Hurricanes with three points to show for it. He had stops in New York and Edmonton over the next three seasons before his NHL career ended.

While it surely wasn’t any kind of blockbuster, it is one of the most recent deals between these two clubs. What do you think of the deals? Were there any clear-cut winners over the years? Be sure to share your thoughts by commenting below and tune in next time to see some of the most recent deals between the Leafs and Blackhawks.