Ron Wilson (2008 – 2012)
Career Record: 648-561-91 with 101 ties; Leafs Record: 130-135-45
Perhaps one of the least successful coaches in shaping the Leafs in the past two decades, Ron Wilson was one of rare ones to sport a losing record during his tenure with the blue and white on this side of the century.
After guiding the Washington Capitals and San Jose Sharks to a plethora of success from 1997 to 2008 including seven playoff appearances and a Stanley Cup berth in 1997-98, his Leafs-led teams never finished higher than fourth in their division nor reached then playoffs.
As a result, he was ultimately fired during the 2011-12 season. Unfortunately for Wilson, that would also be the last time he would be seen as a head coach in the NHL, as his failure with the Leafs probably led to his demise.
Randy Carlyle (2012 – 2015)
Career Record: 475-334-115; Leafs Record: 91-78-19
Randy Carlyle with his Stanley Cup winning pedigree would take over the reigns for the Leafs after the Wilson firing to finish off the 2011-12 season.
The Leafs would finally find a way to briefly flourish under Carlyle’s system, leading to their first playoff appearance in over nine years during the 2012-13 season.
There was a chance that the Leafs could have prospered and gone on to bigger and better things, but we all know what happened in that fateful game 7 against the Boston Bruins after taking a 4-1 lead into the third period.
That would also remain the only year Carlyle was able to lead the Leafs into the postseason, as after another couple mediocre seasons, he was fired in-season during the 2014-15 campaign. Carlyle would actually have his greatest success coaching his only other team to date in the Anaheim Ducks. They made seven playoff appearances over his ten seasons with the club, including capturing the Cup in 2006-07.