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The 1999 NHL Entry Draft was held on Saturday, June 26, 1999 at the Fleet Center, home of the Boston Bruins.
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1999 Pittsburgh Penguins NHL Entry Draft Selections
| Choice | Round | Pick | Overall | Player | Position | 1998-99 Amateur Club |
| 1 | 1 | 23 | 23 | Konstantin Koltsov | LW | Severstal Cherepovets (Russia) |
| 2 | 2 | 23 | 51 | Matt Murley | LW | Rensselaer Polytechnic Institute (NCAA) |
| 3 | 2 | 29 | 57 | Jeremy Van Hoof | D | Ottawa 67's (OHL) |
| 4 | 3 | 20 | 86 | Sebastien Caron | G | Rimouski Oceanic (QMJHL) |
| 5 | 4 | 19 | 115 | Ryan Malone | LW | Omaha Lancers (USHL) |
| 6 | 5 | 18 | 144 | Tomas Skvaridlo | LW | HKm Zvolen Jr. (Slovakia) |
| 7 | 5 | 31 | 157 | Valadimir Malenkikh | D | Tolyatti Lada (Russia) |
| 8 | 6 | 19 | 176 | Doug Meyer | LW | University of Minnesota Golden Gophers (NCAA) |
| 9 | 7 | 18 | 204 | Tom Kostopoulos | RW | London Knights (OHL) |
| 10 | 8 | 18 | 233 | Darcy Robinson | D | Saskatoon Blades (WHL) |
| 11 | 9 | 18 | 261 | Andrew McPherson | LW | Rensselaer Polytechnic Institute (NCAA) |
Konstantin Koltsov |
Matt Murley |
Jeremy Van Hoof |
Sebastien Caron |
Ryan Malone |
Tomas Skvaridlo |
Valadimir Malenkikh |
Doug Meyer |
Tom Kostopoulos |
Darcy Robinson |
Andrew McPherson |