Atlantic:
Tampa
Toronto
Boston
Montreal*
Florida
Buffalo
Detroit
Ottawa

Metropolitan:
Washington
Columbus
New York Islanders
PIttsburgh**
Carolina
Philadelphia
New Jersey Devils
New York Rangers

Central:
Nashville
Winnipeg
St. Louis
Dallas*
Colorado**
Chicago
Minnesota

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

First round:
Tampa over Pittsburgh in 5
Toronto over Boston in 7
Washington over Montreal in 5
Columbus over Islanders in 4

Nashville over Colorado in 6
St louis over Winnipeg in 6
San Jose over Dallas in 4
Calgary over Vegas in 6

2nd Round
Toronto over Tampa in 7
Columbus over Washington in 6

Nashville over St louis in 6
San jose over calgary in 5

Conference Finals
Toronto over Columbus in 7
San Jose over Nashville in 6

Stanley Cup Final
San Jose over Toronto in 6

Awards:
Art Ross: Kucherov
Hart: Kucherov ( P. Kane, Ovechkin
Norris: Giordano ( Burns, Rielly)
Richard: Ovechkin
Calder: Pettersson ( Dahlin, Heiskanen)
Ted Lindsey: Kucherov ( Mcdavid, P. Kane)
Selke: M. Stone ( Crosby, Bergeron )
Vezina: Andersen ( Vasilevksy, Bishop)

Lottery with Picks:
Col via Ott - Jack Hughes
Los Angelas - Kaapo Kakko
Detroit - Kirby Dach

So, San Jose beats Calgary in round 2 but they have a rematch in round 3??????

Not going to make playoff predictions yet, but 1-31 standings predictions:

1 - Tampa Bay - X
2 - Calgary - X
3 - Boston - X
4 - San Jose - X
5 - NY Islanders - X
6 - Toronto - X
7 - Winnipeg - X
8 - Nashville - X
9 - Columbus - X
10 - Washington - X
11 - St. Louis - X
12 - Pittsburgh - X
13 - Vegas - X
14 - Carolina - X
15 - Dallas - X
16 - Montreal
17 - Arizona - X
18 - Minnesota
19 - Colorado
20 - Buffalo
21 - Philadelphia
22 - Florida
23 - Vancouver
24 - Chicago
25 - Edmonton
26 - NY Rangers
27 - Anaheim
28 - New Jersey
29 - Los Angeles
30 - Detroit
31 - Ottawa

There are some bold picks in here, but a lot can change quickly.

Lottery (just for fun) ... used a simulator:

1 - Anaheim
2 - Detroit
3 - Ottawa

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

Metropolitan:
Columbus
New York Islanders
Washington
PIttsburgh*
Carolina
Philadelphia
New York Rangers
New Jersey

Central:
Nashville
Winnipeg
St. Louis
Dallas*
Minnesota**
Colorado
Chicago

Pacific:
Calgary
San Jose
Vegas
Arizona
Vancouver
Edmonton
Anaheim
Los Angeles

First round
Tampa over Montreal in 5
Boston over Toronto in 7
Pittsburgh over Columbus in 6
Washington over Islanders in 6

Nashville over Minnesota in 4
Winnipeg over St. Louis in 6
Calgary over Dallas in 6
Vegas over San Jose in 7

2nd Round
Tampa over Boston in 6
Washington over Pittsburgh in 7

Nashville over Winnipeg in 5
Calgary over Vegas in 7

Conference Finals
Tampa over Washington in 6
Nashville over Calgary in 6

Stanley Cup Final
Tampa over Nashville in 7

Atlantic:
Tampa Bay Lightning
Toronto Maple Leafs
Boston Bruins
Buffalo Sabres**
Florida Panthers
Montreal Canadiens
Detroit Red Wings
Ottawa Senators

Metropolitan:
Columbus Blue Jackets
Washington Capitals
New York Islanders
Pittsburgh Penguins*
Philadelphia Flyers
Carolina Hurricanes
New York Rangers
New Jersey Devils

Central:
Nashville Predators
Winnipeg Jets
St. Louis Blues
Minnesota Wild*
Colorado Avalanche
Dallas Stars
Chicago Blackhawks

Pacific:
San Jose Sharks
Calgary Flames
Vegas Golden Knights
Arizona Coyotes**
Edmonton Oilers
Los Angeles Kings
Anaheim Ducks
Vancouver Canucks

Round 1:
Lightning vs. Sabres (Lightning in 4)
Leafs vs. Bruins (Leafs in 7)
Jackets vs. Penguins (Jackets in 6)
Capitals vs. Islanders (Capitals in 6)

Predators vs. Coyotes (Predators in 4)
Jets vs. Blues (Jets in 6)
Sharks vs. Wild (Sharks in 5)
Flames vs. Knights (Flames in 6)

Round 2:
Lightning vs. Leafs (Lightning in 7)
Jackets vs. Capitals (Jackets in 6)

Predators vs. Jets (Predators in 7)
Sharks vs. Flames (Sharks in 7)

Conference Finals:
Lightning vs. Jackets (Lightning in 6)

Predators vs. Sharks (Predators in 7)

Stanley Cup Final:
Lightning vs. Predators (Lightning in 6)

Atlantic
1. Tampa
2. Boston
3. Toronto
4. Montreal*
5. Buffalo
6. Florida
7. Detroit
8. Ottawa

Metro
1. Washington
2. NY Islanders
3. Columbus
4. Pittsburgh**
5. Carolina
6. Philadelphia
7. NY Rangers
8. New Jersey


Central
1. Winnipeg
2. Nashville
3. St. Louis
4. Colorado*
5. Dallas
6. Minnesota
7. Chicago

Pacific
1. Calgary
2. San Jose
3. Vegas
4. Arizona**
5. Vancouver
6. Edmonton
7. Los Angeles
8. Anaheim


Tampa vs Pittsburgh - Lightning in 6
Boston vs Toronto - Leafs in 7
Washington vs Montreal - Caps in 6
NY Islanders vs Columbus - Jackets in 5

Calgary vs Arizona - Flames in 7
San Jose vs Vegas - Sharks in 7
Winnipeg vs Colorado - Jets in 4
Nashville vs St. Louis - Blues in 5


Tampa vs Toronto - Lightning in 5
Washington vs Columbus - Caps in 7

Calgary vs San Jose - Sharks in 6
Winnipeg vs St. Louis - Jets in 7


Tampa vs Washington - Lightning in 6
San Jose vs Winnipeg - Jets in 7


Tampa vs Winnipeg - Lightning in 7
Conn Smythe: Nikita Kucherov

Taking into account no serious injuries outside of those already on the books. I only concentrated on the teams making the playoffs and not the other 16 teams.


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

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

Central:
Winnipeg
Nashville
St. Louis
Dallas*
Colorado
Chicago
Minnesota

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

First round:
Tampa over Carolina in 6
Boston over Toronto in 6
Montreal over Islanders in 7
Washington over Columbus in 6

Winnipeg over Arizona in 5
Nashville over St Louis in 7
Calgary over Vegas in 6
San Jose over Dallas in 6

2nd Round
Tampa over Montreal in 5
Boston over Washington in 6

Winnipeg over Nashville in 7
San Jose over Calgary in 7

Conference Finals
Tampa over Boston in 6
San Jose over Winnipeg in 7

Stanley Cup Final
Tampa over San Jose in 7

Awards:
Art Ross: Kucherov
Hart: Kucherov ( P. Kane, Ovechkin)
Norris: Giordano ( J Carlson, Burns)
Richard: Ovechkin
Calder: Pettersson ( Dahlin, Heiskanen)
Ted Lindsey: McDavid (Kane, Ovechkin)
Selke: Barkov (Bergeron, Stone)
Vezina: Vaselivski (Bishop, Fleury)

First of all, you're not saying the Isles finish ahead of the Lightning, are you? Because if not, the Isles would play Carolina and the Lightning would play Montreal. I don't see any way the Islanders would finish ahead of Tampa Bay. Also, why do you have Tampa and Montreal playing in the 2nd round? Even if the Isles win every game and the Lightning lose every game (somehow putting the isles ahead of the Lightning), Montreal would play Washington in the 2nd round.

Yeah I messed that up pretty badly. The copy and paste idea didn't work as well as I had hoped. I wish they would go back to the 1 vs 8 format!