The 1999 NHL Draft is defined by Brian Burke’s trade wizardry to land Daniel (#2) and Henrik (#3) Sedin together. Patrik Stefan was the ill-fated #1 pick. The round also featured Tim Connolly (#5) and Nick Boynton (#21). While the first round was generally weak beyond the twins, the late rounds were historic. Henrik Zetterberg was stolen at 210th overall, and Ryan Miller went 139th overall. Martin Erat (191st) and Radim Vrbata (212th) also became long-term NHLers. Overall, 1999 was a draft year of extremes, featuring one of the biggest busts at #1 but also the most successful sibling duo in hockey history.
Career earnings of players picked in the first round of the 1999 NHL entry draft:
| Player | Pos. | Pick # | Drafted by | Career Earnings |
Rank | Career Earnings In today's $ |
Rank |
| Patrik Stefan | C | 1 | Atlanta Thrashers | $6,830,250 | 1685 | $12,074,669 | 1539 |
| Daniel Sedin | LW | 2 | Vancouver Canucks | $78,635,732 | 92 | $112,359,944 | 76 |
| Henrik Sedin | C | 3 | Vancouver Canucks | $78,635,732 | 92 | $112,359,944 | 76 |
| Pavel Brendl | RW | 4 | New York Rangers | $2,949,745 | 2506 | $5,131,837 | 2417 |
| Tim Connolly | C | 5 | New York Islanders | $29,679,650 | 604 | $46,383,812 | 520 |
| Brian Finley | G | 6 | Nashville Predators | $1,025,000 | 3737 | $1,983,176 | 3623 |
| Kris Beech | C | 7 | Washington Capitals | $4,234,745 | 2145 | $7,174,916 | 2038 |
| Taylor Pyatt | LW | 8 | New York Islanders | $13,116,000 | 1156 | $20,566,435 | 1109 |
| Jamie Lundmark | C | 9 | New York Rangers | $3,287,500 | 2398 | $5,479,247 | 2343 |
| Branislav Mezei | D | 10 | New York Islanders | $5,551,000 | 1865 | $9,493,997 | 1774 |
| Oleg Saprykin | LW | 11 | Calgary Flames | $5,553,000 | 1864 | $9,064,464 | 1822 |
| Denis Shvidki | RW | 12 | Florida Panthers | $4,202,500 | 2152 | $7,596,078 | 1989 |
| Jani Rita | LW | 13 | Edmonton Oilers | $450,000 | 4800 | $742,665 | 5047 |
| Jeff Jillson | D | 14 | San Jose Sharks | $2,883,910 | 2535 | $5,078,489 | 2433 |
| David Tanabe | D | 16 | Carolina Hurricanes | $5,775,000 | 1830 | $10,025,961 | 1718 |
| Barret Jackman | D | 17 | St. Louis Blues | $30,878,098 | 585 | $45,503,634 | 540 |
| Konstantin Koltsov | LW | 18 | Pittsburgh Penguins | $627,000 | 4421 | $1,034,780 | 4377 |
| Kirill Safronov | D | 19 | Phoenix Coyotes | $550,000 | 4545 | $963,606 | 4487 |
| Barrett Heisten | LW | 20 | Buffalo Sabres | $1,050,000 | 3710 | $1,911,193 | 3681 |
| Nick Boynton | D | 21 | Boston Bruins | $14,165,000 | 1090 | $22,426,997 | 1045 |
| Steve McCarthy | D | 23 | Chicago Blackhawks | $4,412,500 | 2095 | $7,514,163 | 2000 |
| Martin Havlat | RW | 26 | Ottawa Senators | $46,611,829 | 327 | $70,544,382 | 269 |
| Ari Ahonen | G | 27 | New Jersey Devils | $800,000 | 4101 | $1,401,609 | 4075 |