1999-2000 NHL Season Schedule: May
Monday, May 1st
| Away | Home | Result | |
|---|---|---|---|
 Colorado Avalanche COL | @ |  Detroit Red Wings DET | 1-3 |
 Toronto Maple Leafs TOR | @ |  New Jersey Devils NJ | 1-5 |
Tuesday, May 2nd
| Away | Home | Result | |
|---|---|---|---|
 Philadelphia Flyers PHI | @ |  Pittsburgh Penguins PIT | 4-3 |
 Dallas Stars DAL | @ |  San Jose Sharks SJ | 1-2 |
Wednesday, May 3rd
| Away | Home | Result | |
|---|---|---|---|
Colorado Avalanche COL | @ | Detroit Red Wings DET | 3-2 |
Toronto Maple Leafs TOR | @ | New Jersey Devils NJ | 3-2 |
Thursday, May 4th
| Away | Home | Result | |
|---|---|---|---|
Philadelphia Flyers PHI | @ | Pittsburgh Penguins PIT | 2-1 |
Friday, May 5th
| Away | Home | Result | |
|---|---|---|---|
Detroit Red Wings DET | @ | Colorado Avalanche COL | 2-4 |
Dallas Stars DAL | @ | San Jose Sharks SJ | 5-4 |
Saturday, May 6th
| Away | Home | Result | |
|---|---|---|---|
New Jersey Devils NJ | @ | Toronto Maple Leafs TOR | 4-3 |
Sunday, May 7th
| Away | Home | Result | |
|---|---|---|---|
Pittsburgh Penguins PIT | @ | Philadelphia Flyers PHI | 3-6 |
San Jose Sharks SJ | @ | Dallas Stars DAL | 1-4 |
Monday, May 8th
| Away | Home | Result | |
|---|---|---|---|
Toronto Maple Leafs TOR | @ | New Jersey Devils NJ | 0-3 |
Tuesday, May 9th
| Away | Home | Result | |
|---|---|---|---|
Philadelphia Flyers PHI | @ | Pittsburgh Penguins PIT | 2-1 |
Saturday, May 13th
| Away | Home | Result | |
|---|---|---|---|
Colorado Avalanche COL | @ | Dallas Stars DAL | 2-0 |
Sunday, May 14th
| Away | Home | Result | |
|---|---|---|---|
New Jersey Devils NJ | @ | Philadelphia Flyers PHI | 4-1 |
Monday, May 15th
| Away | Home | Result | |
|---|---|---|---|
Colorado Avalanche COL | @ | Dallas Stars DAL | 2-3 |
Tuesday, May 16th
| Away | Home | Result | |
|---|---|---|---|
New Jersey Devils NJ | @ | Philadelphia Flyers PHI | 3-4 |
Thursday, May 18th
| Away | Home | Result | |
|---|---|---|---|
Philadelphia Flyers PHI | @ | New Jersey Devils NJ | 4-2 |
Friday, May 19th
| Away | Home | Result | |
|---|---|---|---|
Dallas Stars DAL | @ | Colorado Avalanche COL | 0-2 |
Saturday, May 20th
| Away | Home | Result | |
|---|---|---|---|
Philadelphia Flyers PHI | @ | New Jersey Devils NJ | 3-1 |
Sunday, May 21st
| Away | Home | Result | |
|---|---|---|---|
Dallas Stars DAL | @ | Colorado Avalanche COL | 4-1 |
Monday, May 22nd
| Away | Home | Result | |
|---|---|---|---|
New Jersey Devils NJ | @ | Philadelphia Flyers PHI | 4-1 |
Tuesday, May 23rd
| Away | Home | Result | |
|---|---|---|---|
Colorado Avalanche COL | @ | Dallas Stars DAL | 2-3 |
Wednesday, May 24th
| Away | Home | Result | |
|---|---|---|---|
Philadelphia Flyers PHI | @ | New Jersey Devils NJ | 1-2 |
Thursday, May 25th
| Away | Home | Result | |
|---|---|---|---|
Dallas Stars DAL | @ | Colorado Avalanche COL | 1-2 |
Friday, May 26th
| Away | Home | Result | |
|---|---|---|---|
New Jersey Devils NJ | @ | Philadelphia Flyers PHI | 2-1 |
Saturday, May 27th
| Away | Home | Result | |
|---|---|---|---|
Colorado Avalanche COL | @ | Dallas Stars DAL | 2-3 |
Tuesday, May 30th
| Away | Home | Result | |
|---|---|---|---|
Dallas Stars DAL | @ | New Jersey Devils NJ | 3-7 |
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