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1999 - Round: 5
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| Round | Pick | Overall | Team | Player | Pos | Country | Ht | Wt | Amateur League | Amateur Team |
| 5 | 1 | 127 | TBL | Kaspars Astashenko | D | LVA | 6' 1" | 206 | Lavtia | Riga |
| 5 | 2 | 128 | ATL | Derek MacKenzie | C | CAN | 5' 11" | 178 | OHL | Sudbury Wolves |
| 5 | 3 | 129 | VAN | Ryan Thorpe | L | CAN | 6' 4" | 202 | WHL | Spokane Chiefs |
| 5 | 4 | 130 | NYI | Justin Mapletoft | C | CAN | 6' 1" | 202 | WHL | Red Deer Rebels |
| 5 | 5 | 131 | NSH | Konstantin Panov | R | RUS | 6' 0" | 186 | WHL | Kamloops Blazers |
| 5 | 6 | 132 | WSH | Roman Tvrdon | C | SVK | 6' 1" | 197 | Slovakia | Trencin Jr. |
| 5 | 7 | 133 | LAK | Jean-Francois Nogues | G | CAN | 6' 2" | 154 | QMJHL | Victoriaville Tigres |
| 5 | 8 | 134 | CHI | Michael Jacobsen | D | CAN | 6' 0" | 207 | OHL | Belleville Bulls |
| 5 | 9 | 135 | CGY | Matt Doman | R | USA | 6' 0" | 218 | NCAA | U. of Wisconsin |
| 5 | 10 | 136 | MTL | Dustin Jamieson | L | CAN | 6' 2" | 180 | OHL | Sarnia Sting |
| 5 | 11 | 137 | NYR | Garett Bembridge | R | CAN | 6' 0" | 164 | WHL | Saskatoon Blades |
| 5 | 12 | 138 | BUF | Ryan Miller | G | USA | 6' 2" | 175 | NAHL | Soo Indians |
| 5 | 13 | 139 | EDM | Jonathan Fauteux | D | CAN | 6' 2" | 232 | QMJHL | Val-d'Or Foreurs |
| 5 | 14 | 140 | NYI | Adam Johnson | D | USA | 6' 6" | 220 | Minn H.S. | Greenway |
| 5 | 15 | 141 | ANA | Maxim Rybin | R | RUS | 5' 9" | 167 | Russia | Moscow Spartak |
| 5 | 16 | 142 | COL | William Magnuson | D | USA | 6' 5" | 232 | NCAA | Lake Superior State University |
| 5 | 17 | 143 | STL | Trevor Byrne | D | USA | 6' 3" | 200 | Mass H.S. | Deerfield Academy |
| 5 | 18 | 144 | PIT | Tomas Skvaridlo | C | SVK | 6' 1" | 180 | Slovakia | Zvolen Jr. |
| 5 | 19 | 145 | MTL | Marc-Andre Thinel | R | CAN | 5' 11" | 158 | QMJHL | Victoriaville Tigres |
| 5 | 20 | 146 | BUF | Matthew Kinch | D | CAN | 5' 11" | 185 | WHL | Calgary Hitmen |
| 5 | 21 | 147 | BOS | Seamus Kotyk | G | CAN | 5' 11" | 180 | OHL | Ottawa 67's |
| 5 | 22 | 148 | TBL | Michal Lanicek | G | CZE | 6' 1" | 172 | Czech | Slavia Praha Jr. |
| 5 | 23 | 149 | DET | Andrei Maximenko | L | RUS | 5' 11" | 172 | Russia | Krylja Sovetov |
| 5 | 24 | 150 | MTL | Matt Shasby | D | USA | 6' 2" | 188 | USHL | Des Moines Buccaneers |
| 5 | 25 | 151 | TOR | Vaclav Zavoral | D | CZE | 6' 3" | 198 | Czech. | Litvinov Jr. |
| 5 | 26 | 152 | COL | Jordan Krestanovich | L | CAN | 6' 0" | 170 | WHL | Calgary Hitmen |
| 5 | 27 | 153 | CGY | Jesse Cook | D | USA | 6' 6" | 210 | NCAA | U. of Denver |
| 5 | 28 | 154 | OTT | Andrew Ianiero | L | CAN | 6' 0" | 188 | OHL | Kingston Frontenacs |
| 5 | 29 | 155 | SJS | Nicholas Dimitrakos | R | USA | 5' 11" | 193 | NCAA | U. of Maine |
| 5 | 30 | 156 | DAL | Gregor Baumgartner | R | AUT | 6' 2" | 185 | QMJHL | Acadie-Bathurst Titan |
| 5 | 31 | 157 | PIT | Vladimir Malenkykh | D | RUS | 6' 1" | 187 | Russia | Tolyatti Lada |
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