Five trades over a span of the last 12 years and that’s the extent to which the Toronto Maple Leafs have had dealings with the Arizona Coyotes’ franchise. While they haven’t made a move in the past year and a half, the two teams did engage in five trades over the past 10 years.

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

Hailing Holland

While Peter Holland did play 174 games for the Maple Leafs during the regular season, he wasn’t a constant for the team. That’s why he reportedly became unhappy with the club which led to the Leafs trading the forward to the Coyotes.

Holland has bounced from team to team, and was moved by the Leafs to Arizona in 2016. (Dan Hamilton-USA TODAY Sports)

The Leafs received a 2018 conditional sixth-round pick in return for Holland on Dec. 9, 2016. The condition was that the Leafs would receive a sixth-rounder if the Coyotes were able to sign or trade Holland who was a pending restricted free agent at the time.

Neither condition was met and the Leafs won’t receive a pick from the Coyotes in the upcoming draft.

Related: Leafs Give Holland a Chance With Coyotes

Lombardi Becomes Coyote

While the Leafs didn’t get a pick in the Holland deal, they did acquire a 2014 fourth-round pick in a deal with the Coyotes on Jan. 16, 2013, when they moved Matthew Lombardi to the desert.

Lombardi played just 21 games for the Coyotes – who at the time were known for the Phoenix Coyotes. Over that span he collected eight points. That was his second tenure with the team and he was quickly moved to Anaheim.

The Maple Leafs drafted J.J. Piccinich as a result of the Lombardi trade. (Photo by Terry Wilson/OHL Images)

The Leafs, on the other hand, used the fourth-round pick to take former London Knight captain – J.J. Piccinich – 103rd overall in the 2014 NHL Entry Draft. While he has yet to play a game with the Leafs, he has seen some success with the team’s ECHL affiliate – the Orlando Solar Bears. In 54 games with the Bears, he has 14 goals and 32 points, but remains a minus-15 this season.

Sending Away Stempniak

After playing 123 regular season games for the Leafs over parts of two seasons in which he accumulated 25 goals and 61 points, Lee Stempniak was shipped out to the Coyotes on Mar. 3, 2010, by the Maple Leafs.

In return, the Leafs acquired defenceman Matt Jones along with a 2010 fourth-round pick and a 2010 seventh-round pick. Jones never played a game for the Leafs and hasn’t played an NHL game since 2007-08 with the Coyotes. In fact, he last played in the AHL in 2008-09 with the San Antonio Rampage.

As for the picks, the Leafs eventually traded the fourth-rounder to Washington who used it to take Philipp Grubauer 112th overall and they traded the seventh-rounder to Edmonton who used it to take Kellen Jones 202nd overall.

Third Time’s Not a Charm

Originally drafted by the Leafs and having a second stint midway through his career, the Leafs re-acquired centre Yanic Perreault along with a 2008 fifth-round pick from the Coyotes on Feb. 27, 2007. In exchange, the Coyotes get defenceman Brendan Bell and a 2008 second-round pick.

Perreault played 17 games with the Leafs following the deal tallying five points over that span. He finished his career with a season in Chicago before retiring from the NHL. As for the pick, the Leafs used it to take Joel Champagne with the 129th overall pick in 2008. Champagne is currently playing in France with Grenoble where he has 56 points in 44 games.

As for the Coyotes, Bell played 16 games for the team with two assists to show for it. The second-round pick was eventually moved to Nashville who used it to pick current captain Roman Josi who has been a staple on the Predators blue line since he debuted in the NHL. Josi is signed through the 2019-20 season.

Tellqvist, Not Their Guy

Finally, the Leafs engaged in a trade with the Coyotes on Nov. 27, 2006, when they shipped goaltender Mikael Tellqvist to Arizona for Tyson Nash and a 2007 fourth-round pick.

The Leafs drafted Matt Frattin as a result of the Tellqvist deal. (Charles LeClaire-USPRESSWIRE)

Tellqvist played 67 games for the Coyotes after the trade and collected a 27-24-6 record with a .897 save percentage and 3.06 goals against average over that span. He last played with Buffalo during the 2008-09 season after being traded by the Coyotes.

On the Leafs side, Nash never played a game for the team. In fact, the trade ended his NHL career. As for the pick, the Leafs used it to pick Matt Frattin with the 99th overall pick. Frattin’s played 91 career games for the Leafs totalling 15 goals and 28 points. Since then, however, he’s been forced out to Europe playing both in the Swiss League and the KHL.

Are there legitimate winners and losers in any of these trades? Be sure to share your thoughts below and tune in next time for some of the most recent action between the Maple Leafs and their division rival Boston Bruins.