1999 Major League Baseball Draft First round selections First round selections

| Pick | Player | Team | Position_ | School |
|---|---|---|---|---|
| 19 | Alex Ríos | Toronto Blue Jays | OF | San Pedro Martin HS (Guaynabo, PR) |
| 20 | Vince Faison | San Diego Padres | OF | Toombs County HS (Lyons, Georgia) |
| 21 | Larry Bigbie | Baltimore Orioles | OF | Ball State University |
| 22 | Matt Ginter | Chicago White Sox | P | Mississippi State University |
| 23 | Keith Reed | Baltimore Orioles | OF | Providence College |
| 24 | Kurt Ainsworth | San Francisco Giants | P | Louisiana State University |
| 25 | Mike MacDougal | Kansas City Royals | P | Wake Forest University |
| 26 | Ben Christensen | Chicago Cubs | P | Wichita State University |
| 27 | David Walling | New York Yankees | P | University of Arkansas |
| 28 | Gerik Baxter | San Diego Padres | P | Edmonds Woodway HS (Edmonds, Washington) |