First Round:

Tampa Bay vs Philadelphia (Tampa wins in 4)
Pittsburgh vs Florida (Florida wins in 7)
Boston vs Toronto (Boston wins in 6)
Washington vs Columbus (Columbus wins in 5)

Nashville vs Anaheim (Nashville wins in 7)
Vegas vs Colorado (Colorado wins in 5)
Winnipeg vs Minnesota (Winnipeg wins in 4)
San Jose vs Los Angeles (Los Angeles wins in 7)

Second Round:

Tampa Bay vs Florida (Florida wins in 7)
Boston vs Columbus (Boston wins in 5)

Nashville vs Colorado (Colorado wins in 7)
Winnipeg vs Los Angeles (Winnipeg wins in 6)

Conference Finals:

Boston vs Florida (Boston wins in 7)

Winnipeg vs Colorado (Winnipeg wins in 5)

Stanley Cup Finals:

Boston vs Winnipeg (Winnipeg wins in 7)

As of right now, here are my predictions:

Buffalo vs. Florida (Buffalo in 4)
Montreal vs. Ottawa (Montreal in 5)
NY Rangers vs. Detroit (Detroit in 6)
Carolina vs. NY Islanders (NY Islanders in 7)
Chicago vs. Calgary (Calgary in 7)
St. Louis vs. Colorado (Colorado in 7)
Arizona vs. Anaheim (Arizona in 5)
Vancouver vs. Edmonton (Vancouver in 4)

Buffalo vs. Montreal (Montreal in 6)
NY Islanders vs. Detroit (Detroit in 6)
Colorado vs. Calgary (Calgary in 6)
Arizona vs. Vancouver (Arizona in 5)

Montreal vs. Detroit (Montreal in 7)
Arizona vs. Calgary (Arizona in 6)

Arizona vs. Montreal (Arizona in 6)

----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Tampa Bay vs. New Jersey (Tampa Bay in 6)
Boston vs. Toronto (Toronto in 7)
Washington vs. Columbus (Washington in 6)
Pittsburgh vs. Philadelphia (Philadelphia in 7)
Nashville vs. Colorado (Nashville in 6)
Winnipeg vs. Dallas (Winnipeg in 7)
Vegas vs. Minnesota (Vegas in 5)
San Jose vs. Los Angeles (Los Angeles in 5)

Tampa Bay vs. Toronto (Tampa Bay in 7)
Washington vs. Philadelphia (Washington in 5)
Nashville vs. Winnipeg (Nashville in 6)
Vegas vs. Los Angeles (Vegas in 7)

Tampa Bay vs. Washington (Tampa Bay in 7)
Nashville vs. Vegas (Nashville in 7)

Tampa Bay vs. Nashville (Tampa Bay in 6)

Not to be the rampant Pens fan here... But a team that's 8-0 in playoff series over the last two years, and one of the hottest teams in the league since January, and you both have them getting knocked out in the first round (especially by Florida)?

Tampa Bay vs. Columbus (Tampa is 5)
Boston vs. Toronto (Boston in 7)
Washington vs. Philadelphia (Washington in 6)
Pittsburgh vs. New Jersey (Pittsburgh in 7)
Nashville vs. Anaheim (Nashville in 5)
Winnipeg vs. Minnesota (Winnipeg in 5)
Vegas vs. Dallas (Dallas in 7)
San Jose vs. Los Angeles (San Jose in 7)

Tampa vs. Boston (Boston in 7)
Washington vs. Pittsburgh (Pittsburgh in 7)
Nashville vs. Winnipeg (Nashville in 6)
San Jose vs. Dallas (Dallas in 6)

Boston vs Pittsburgh (Boston in 6)
Nashville vs Dallas (Nashville in 6)

Boston vs. Nashville (Boston in 6)

Very interesting!!!

Wow, very interesting!!!

That's why I'm calling them bold predictions. I wouldn't bet on them, but I could see something very similar happening. The best regular season teams rarely do well in the playoffs and it's sometimes a team who sneaks in on the last day of the season who wins it all.

tampa over NJ in 5
Toronto over Boston in 7
Washington over Columbus in 6
philadelphia over pittsburgh in 6
Nashville over Anaheim in 6
Winnipeg over Minnesota in 4
Vegas over Dallas in 7
Los Angeles over San Jose in 7

Tampa over Toronto in 7
Washington over Philadelphia in 5
Winnipeg over Nashville in 6
Los Angelas over Vegas in 6

Tampa over Washington in 7
Winnipeg over LA in 5

Winnipeg over Tampa in 7

I like Tony's bold predictions; here's my not-so-bold predictions.

TBL 4 - 3 FLA
BOS 4 - 2 TOR
WSH 4 - 1 CBJ
PIT 4 - 3 PHI
NSH 4 - 1 COL
WPG 4 - 0 MIN
VGK 4 - 3 DAL
LAK 4 - 2 SJS

BOS 4 - 3 TBL
PIT 4 - 2 WSH
NSH 4 - 3 WPG
VGK 4-1 LAK

PIT 4 - 2 BOS
NSH 4 - 2 VGK

NSH 4 - PIT 3

A rematch of last year's cup final ... I like this end better than last year's

Tampa Bay vs. Columbus (Tampa in 5)
Boston vs. Toronto (Boston in 6)
Washington vs. New Jersey (Washington in 6)
Pittsburgh vs. Philadelphia (Pittsburgh in 5)
Nashville vs. Anaheim (Nashville in 6)
Winnipeg vs. Minnesota (Winnipeg in 6)
Vegas vs. Colorado (Vegas in 7)
San Jose vs. Los Angeles (Los Angeles in 6)

Tampa vs. Boston (Tampa in 7)
Washington vs. Pittsburgh (Pittsburgh in 7)
Nashville vs. Winnipeg (Nashville in 6)
Vegas vs. Los Angeles (Los Angeles in 6)

Tampa vs Pittsburgh (Tampa in 7)
Nashville vs Los Angeles (Nashville in 6)

Tampa vs. Nashville (Nashville in 7)

This isn’t even possible, Nashville would play Winnipeg, Colorado would play LA, Columbus would play Florida, and Tampa Bay would play Boston.

With all these different predictions, this playoff looks very unpredictable. So many people predicting very different things.

Not really bold but I'll take a crack at this:

First Round:

Tampa Bay vs New Jersey (Tampa in 6)
Boston vs Toronto (Toronto in 7)
Washington vs Columbus (Washington in 5)
Pittsburgh vs Philadelphia (Pittsburgh in 6)

Nashville vs Anaheim (Nashville in 7)
Winnipeg vs Minnesota (Winnipeg in 4)
Vegas vs Colorado (Vegas in 6)
San Jose vs Los Angeles (LA in 5)

Second Round:

Tampa Bay vs Toronto (Tampa in 6)
Washington vs Pittsburgh (Washington in 5)

Nashville vs Winnipeg (Winnipeg in 7)
Vegas vs LA (Vegas in 7)

Third Round:

Tampa vs Washington (Washington in 7) (don't judge I'm tryna make it bold here)
Winnipeg vs Vegas (Winnipeg in 6)

Stanley Cup Finals:

Washington vs Winnipeg (Winnipeg in 7)

Stanley Cup Winner: Winnipeg Jets
Conn Smythe: Blake Wheeler

Yes! Yess! YYEEESSS!

After doing some heavy thinking and discussion with @mhockey91 This could most likely be a possible scenario this year. Since when are the playoffs perfect when the best teams in the season move onto the finals right?

Final Standings in

Atlantic:
Tampa
Boston
Toronto
Florida**
Detroit
Montreal
Ottawa
Buffalo

Metro:
Washington
Pittsburgh
Columbus
Philadelphia*
Carolina
New Jersey
New York Rangers
New York Islanders

Central:
Nashville
Winnipeg
Minnesota
Colorado*
Dallas
St Louis
Chicago

Pacific:
Vegas
Los angelas
San Jose
Anaheim**
Calgary
Edmonton
Arizona
Vancouver

First Round:

Tampa over Florida in 5
Toronto over Boston in 7
Washington over Philadelphia in 6
Pittsburgh over Columbus in 7
Nashville over Anaheim in 6
Minnesota over Winnipeg in 7
Colorado over Vegas in 7
Los Angelas over San Jose in 6

Second Round:

Tampa over Toronto in 7
Pittsburgh over Washington in 6
Minnesota over Nashville in 7
Los Angelas over Colorado in 6

Conference Finals:

Pittsburgh over Tampa in 7
Los Angelas over Minnesota in 6

Cup Finals

Los Angelas over Pittsburgh in 7

Atlantic:
Tampa
Boston
Toronto
Florida
Detroit
Montreal
Ottawa
Buffalo

Metro:
Washington
Pittsburgh
Columbus
Philadelphia*
New Jersey **
Carolina
New York Rangers
New York Islanders

Central:
Nashville
Winnipeg
Minnesota
Colorado*
Dallas
St Louis
Chicago

Pacific:
Vegas
San Jose
Anaheim
Los Angelas **
Calgary
Edmonton
Arizona
Vancouver

First Round:

Tampa over NJ in 6
Boston over Toronto in 7
Washington over Philadelphia in 7
Pittsburgh over Columbus in 5

LA over Nashville in 6
Winnipeg over Minnesota in 6
Vegas over Colorado in 5
Anaheim over SJ in 7

Second Round

Boston over Tampa in 7
Washington over Pittsburgh in 7

LA over Winnipeg in 7
Anaheim over Vegas in 6

Conference Finals

Boston over Washington in 7

Anaheim over LA in 6

Cup Finals

Anaheim over Boston in 6