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1999 - Round: 2
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| Round | Pick | Overall | Team | Player | Pos | Country | Ht | Wt | Amateur League | Amateur Team |
| 2 | 1 | 29 | WSH | Michal Sivek | C | CZE | 6' 3" | 213 | Czech Senior League | |
| 2 | 2 | 30 | ATL | Luke Sellars | D | CAN | 6' 1" | 210 | OHL | Ottawa 67's |
| 2 | 3 | 31 | WSH | Charlie Stephens | C | CAN | 6' 4" | 225 | OHL | Guelph Storm |
| 2 | 4 | 32 | DAL | Michael Ryan | C | USA | 6' 1" | 188 | Mass. | Boston College High |
| 2 | 5 | 33 | NSH | Jonas Andersson | R | SWE | 6' 3" | 204 | Sweden | |
| 2 | 6 | 34 | WSH | Ross Lupaschuk | D | CAN | 6' 1" | 218 | WHL | Prince Albert Raiders |
| 2 | 7 | 35 | BUF | Milan Bartovic | R | SVK | 5' 11" | 197 | Slovakia | |
| 2 | 8 | 36 | EDM | Alexei Semenov | D | RUS | 6' 6" | 245 | OHL | Sudbury Wolves |
| 2 | 9 | 37 | WSH | Nolan Yonkman | D | CAN | 6' 6" | 253 | WHL | Kelowna Rockets |
| 2 | 10 | 38 | CGY | Dan Cavanaugh | C | USA | 6' 1" | 190 | NCAA | Boston University |
| 2 | 11 | 39 | MTL | Alexander Buturlin | L | RUS | 5' 11" | 183 | Russia | CSKA Jr. |
| 2 | 12 | 40 | FLA | Alex Auld | G | CAN | 6' 4" | 216 | OHL | North Bay Centennials |
| 2 | 13 | 41 | EDM | Tony Salmelainen | L | FIN | 5' 9" | 185 | FNL | HIFK Helsinki |
| 2 | 14 | 42 | NJD | Mike Commodore | D | CAN | 6' 4" | 233 | NCAA | U. of North Dakota |
| 2 | 15 | 43 | LAK | Andrei Shefer | L | RUS | 6' 1" | 194 | Russia | Cherepovets Severstal |
| 2 | 16 | 44 | ANA | Jordan Leopold | D | USA | 6' 1" | 206 | NCAA | U. of Minnesota |
| 2 | 17 | 45 | COL | Martin Grenier | D | CAN | 6' 5" | 245 | QMJHL | Quebec Remparts |
| 2 | 18 | 46 | CHI | Dimitri Levinski | R | KAZ | 6' 1" | 183 | Russia | Cherepovets Severstal |
| 2 | 19 | 47 | TBL | Sheldon Keefe | R | CAN | 5' 11" | 185 | OHL | Barrie Colts |
| 2 | 20 | 48 | OTT | Simon Lajeunesse | G | CAN | 6' 1" | 178 | QMJHL | Moncton Wildcats |
| 2 | 21 | 49 | CAR | Brett Lysak | C | CAN | 6' 0" | 190 | WHL | Regina Pats |
| 2 | 22 | 50 | NJD | Brett Clouthier | L | CAN | 6' 4" | 215 | OHL | Kingston Frontenacs |
| 2 | 23 | 51 | PIT | Matt Murley | L | USA | 6' 2" | 206 | NCAA | R.P.I. |
| 2 | 24 | 52 | NSH | Adam Hall | R | USA | 6' 3" | 213 | NCAA | Michigan State University |
| 2 | 25 | 53 | PHX | Brad Ralph | L | CAN | 6' 2" | 198 | OHL | Oshawa Generals |
| 2 | 26 | 54 | NSH | Andrew Hutchinson | D | USA | 6' 2" | 195 | NCAA | Michigan State University |
| 2 | 27 | 55 | BUF | Doug Janik | D | USA | 6' 2" | 211 | NCAA | U. of Maine |
| 2 | 28 | 56 | BOS | Matt Zultek | C | CAN | 6' 4" | 222 | OHL | Ottawa 67's |
| 2 | 29 | 57 | PIT | Jeremy Van Hoof | D | CAN | 6' 2" | 200 | OHL | Ottawa 67's |
| 2 | 30 | 58 | MTL | Matt Carkner | D | CAN | 6' 4" | 238 | OHL | Peterborough Petes |
| 2 | 31 | 59 | NYR | David Inman | L | USA | 6' 1" | 180 | NCAA | Notre Dame |
| 2 | 32 | 60 | TOR | Peter Reynolds | D | CAN | 6' 3" | 195 | OHL | London Knights |
| 2 | 33 | 61 | NSH | Ed Hill | D | USA | 6' 2" | 215 | OHL | Barrie Colts |
| 2 | 34 | 62 | OTT | Teemu Sainomaa | L | FIN | 6' 3" | 202 | Finland | Jokerit Jrs |
| 2 | 35 | 63 | CHI | Stepan Mokhov | D | KAZ | 6' 1" | 183 | Russia | Cherepovets Severstal |
| 2 | 36 | 64 | BUF | Mike Zigomanis | C | CAN | 6' 0" | 200 | OHL | Kingston Frontenacs |
| 2 | 37 | 65 | NSH | Jan Lasak | G | SVK | 6' 0" | 204 | Slovak | Zvolen HKm |
| 2 | 38 | 66 | DAL | Dan Jancevski | D | CAN | 6' 3" | 222 | OHL | London Knights |
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