2020:
In 2020, the Leafs lost to the Columbus Blue Jackets in the qualifying round. The Blue Jackets were then subsequently defeated by the eventual champions, the Tampa Bay Lightning.
2021:
2021 saw the Leafs failed to advance in past round one (again), but this time fell to eventual finalist, the Montreal Canadiens. The Habs fell in five games in the Stanley Cup Final to the Tampa Bay Lightning, who won their second Cup in a row.
2022:
In 2022, the Leafs took on the previously mentioned Lightning, and while they put out a strong performance, they fell short in game seven yet again.
The Lightning then lost in the Stanley Cup Final to the Colorado Avalanche, ending their pursuit of a third-straight championship.
2023:
This was the year the Leafs finally made it to round two, but their time was short lived. They lost in five games to the Florida Panthers, who then lost to eventual champions, the Vegas Golden Knights in the Stanley Cup Final.
2024:
After a five-year hiatus, the Leafs took on the Bruins in round one yet again. After another game seven loss to their rivals, Boston then took on the Florida Panthers in round two, who defeated the Bruins and went on to win their first Stanley Cup in franchise history.
In short, it's safe to say the Leafs have played some phenomenal teams in recent playoff years. Now, would the Leafs have defeated these eventual champions had they played them? Likely not, but it's always fun to speculate.
Regardless, when the Leafs do eventually win that elusive Stanley Cup, it'll be even sweeter.