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| First Round Draft Pick History |
| 1 | 12 | 12 | 2000 | Annual Draft | P | Jon | Garland | MLB |
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| 1 | 17 | 17 | 2000 | Annual Draft | 3B | Aubrey | Huff | MLB |
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| 1 | 8 | 8 | 1999 | Annual Draft | OF | Vernon | Wells | MLB |
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| 1 | 13 | 13 | 1998 | Annual Draft | 3B | Mike | Lowell | MLB |
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| 1 | 14 | 14 | 1998 | Annual Draft | P | Orlando | Hernandez | MLB |
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| 1 | 12 | 12 | 1997 | Annual Draft | 1B | Paul | Konerko | MLB |
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| 1 | 17 | 17 | 1995 | Inaugural Draft | P | Tom | Glavine | MLB |
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| Complete Draft History |
| 1 | 12 | 12 | 2000 | Annual Draft | P | Jon | Garland | MLB |
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| 1 | 17 | 17 | 2000 | Annual Draft | 3B | Aubrey | Huff | MLB |
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| 2 | 12 | 36 | 2000 | Annual Draft | P | Jason | Grilli | MLB |
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| 3 | 12 | 60 | 2000 | Annual Draft | P | Carlos | Perez | MLB |
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| 4 | 12 | 84 | 2000 | Annual Draft | P | Tony | McKnight | MLB |
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| 5 | 12 | 108 | 2000 | Annual Draft | P | Joe | Slusarski | MLB |
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| 6 | 12 | 132 | 2000 | Annual Draft | SS | Tomas | De La Rosa | MLB |
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| 7 | 12 | 156 | 2000 | Annual Draft | 1B | Alex | Cabrera | MLB |
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| 1 | 8 | 8 | 1999 | Annual Draft | OF | Vernon | Wells | MLB |
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| 2 | 8 | 32 | 1999 | Annual Draft | P | Ryan | Franklin | MLB |
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| 3 | 8 | 56 | 1999 | Annual Draft | C | Jose | Molina | MLB |
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| 4 | 8 | 80 | 1999 | Annual Draft | P | Nelson | Cruz | MLB |
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| 5 | 8 | 104 | 1999 | Annual Draft | P | Jeremy | Powell | MLB |
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| 6 | 8 | 128 | 1999 | Annual Draft | P | Aaron | Myette | MLB |
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| 7 | 8 | 152 | 1999 | Annual Draft | OF | Tim | Hyers | MLB |
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| 8 | 8 | 176 | 1999 | Annual Draft | P | Andrew | Lorraine | MLB |
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| 9 | 8 | 200 | 1999 | Annual Draft | P | Matt | Perisho | MLB |
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| 1 | 13 | 13 | 1998 | Annual Draft | 3B | Mike | Lowell | MLB |
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| 1 | 14 | 14 | 1998 | Annual Draft | P | Orlando | Hernandez | MLB |
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| 2 | 13 | 37 | 1998 | Annual Draft | P | Bob | Howry | MLB |
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| 2 | 14 | 38 | 1998 | Annual Draft | P | Odalis | Perez | MLB |
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| 2 | 23 | 47 | 1998 | Annual Draft | P | Justin | Speier | MLB |
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| 4 | 5 | 77 | 1998 | Annual Draft | 2B+ | Joe | McEwing | MLB |
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| 5 | 5 | 101 | 1998 | Annual Draft | P | Brad | Woodall | MLB |
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| 6 | 5 | 125 | 1998 | Annual Draft | P | Chris | Brock | MLB |
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| 6 | 13 | 133 | 1998 | Annual Draft | C | Brian | Banks | MLB |
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| 7 | 5 | 149 | 1998 | Annual Draft | P | Dave | Telgheder | MLB |
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| 7 | 13 | 157 | 1998 | Annual Draft | 2B | Donnie | Sadler | MLB |
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| 8 | 5 | 173 | 1998 | Annual Draft | SS | Mendy | Lopez | MLB |
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| 16 | 13 | 373 | 1998 | Annual Draft | P | Joe | Fontenot | MLB |
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| 1 | 12 | 12 | 1997 | Annual Draft | 1B | Paul | Konerko | MLB |
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| 2 | 23 | 47 | 1997 | Annual Draft | OF | Juan | Encarnacion | MLB |
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| 3 | 23 | 71 | 1997 | Annual Draft | 2B | Tripp | Cromer | MLB |
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| 3 | 24 | 72 | 1997 | Annual Draft | P | Dennys | Reyes | MLB |
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| 4 | 23 | 95 | 1997 | Annual Draft | P | Scott | Bailes | MLB |
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| 5 | 23 | 119 | 1997 | Annual Draft | P | Shayne | Bennett | MLB |
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| 5 | 24 | 120 | 1997 | Annual Draft | P | Rob | Stanifer | MLB |
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| 6 | 23 | 143 | 1997 | Annual Draft | P | Robinson | Checo | MLB |
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| 3 | 12 | 60 | 1996 | Annual Draft | C | Keith | Osik | MLB |
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| 3 | 18 | 66 | 1996 | Annual Draft | OF | Jermaine | Allensworth | MLB |
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| 4 | 18 | 90 | 1996 | Annual Draft | P | Jerry | Spradlin | MLB |
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| 5 | 18 | 114 | 1996 | Annual Draft | OF | Brooks | Kieschnick | MLB |
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| 6 | 18 | 138 | 1996 | Annual Draft | SS | Wilson | Delgado | MLB |
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| 7 | 18 | 162 | 1996 | Annual Draft | P | Dan | Carlson | MLB |
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| 8 | 18 | 186 | 1996 | Annual Draft | P | Curt | Lyons | MLB |
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| 9 | 18 | 210 | 1996 | Annual Draft | P | Tom | Thobe | MLB |
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| 10 | 18 | 234 | 1996 | Annual Draft | 1B+ | Dan | Peltier | MLB |
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| 11 | 18 | 258 | 1996 | Annual Draft | OF | Keith | Mitchell | MLB |
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| 12 | 18 | 282 | 1996 | Annual Draft | OF | Terry | Bradshaw | MLB |
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| 13 | 18 | 306 | 1996 | Annual Draft | P | Al | Osuna | MLB |
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| 14 | 18 | 330 | 1996 | Annual Draft | P | Larry | Mitchell | MLB |
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| 1 | 17 | 17 | 1995 | Inaugural Draft | P | Tom | Glavine | MLB |
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| 2 | 8 | 32 | 1995 | Inaugural Draft | 1B | Rafael | Palmeiro | MLB |
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| 3 | 17 | 65 | 1995 | Inaugural Draft | P | Denny | Neagle | MLB |
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| 4 | 8 | 80 | 1995 | Inaugural Draft | 3B | Travis | Fryman | MLB |
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| 5 | 17 | 113 | 1995 | Inaugural Draft | C | Brad | Ausmus | MLB |
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| 6 | 8 | 128 | 1995 | Inaugural Draft | SS | Jay | Bell | MLB |
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| 7 | 17 | 161 | 1995 | Inaugural Draft | OF | Jeff | Conine | MLB |
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| 8 | 8 | 176 | 1995 | Inaugural Draft | OF | Lance | Johnson | MLB |
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| 9 | 17 | 209 | 1995 | Inaugural Draft | P | Ken | Hill | MLB |
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| 10 | 8 | 224 | 1995 | Inaugural Draft | 3B | Jeff | King | MLB |
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| 11 | 17 | 257 | 1995 | Inaugural Draft | P | Erik | Hanson | MLB |
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| 13 | 17 | 305 | 1995 | Inaugural Draft | OF | Geronimo | Berroa | MLB |
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| 13 | 24 | 312 | 1995 | Inaugural Draft | P | Mike | Morgan | MLB |
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| 14 | 1 | 313 | 1995 | Inaugural Draft | P | Chris | Haney | MLB |
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| 14 | 8 | 320 | 1995 | Inaugural Draft | P | Mel | Rojas | MLB |
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| 15 | 17 | 353 | 1995 | Inaugural Draft | C | Eddie | Taubensee | MLB |
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| 16 | 8 | 368 | 1995 | Inaugural Draft | P | Greg A. | Harris | MLB |
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| 17 | 17 | 401 | 1995 | Inaugural Draft | OF | Tom | Goodwin | MLB |
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| 18 | 8 | 416 | 1995 | Inaugural Draft | P | T.J. | Mathews | MLB |
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| 19 | 17 | 449 | 1995 | Inaugural Draft | P | Dennis | Eckersley | MLB |
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| 20 | 8 | 464 | 1995 | Inaugural Draft | SS | Ozzie | Guillen | MLB |
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| 21 | 17 | 497 | 1995 | Inaugural Draft | P | Toby | Borland | MLB |
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| 23 | 17 | 545 | 1995 | Inaugural Draft | P | Pedro | Borbon | MLB |
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| 24 | 8 | 560 | 1995 | Inaugural Draft | 2B | Jason | Bates | MLB |
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| 25 | 17 | 593 | 1995 | Inaugural Draft | P | Jay | Powell | MLB |
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| 26 | 8 | 608 | 1995 | Inaugural Draft | P | Mark | Dewey | MLB |
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| 27 | 17 | 641 | 1995 | Inaugural Draft | C | Mike | LaValliere | MLB |
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| 28 | 8 | 656 | 1995 | Inaugural Draft | OF+ | Jerald | Clark | MLB |
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| 29 | 17 | 689 | 1995 | Inaugural Draft | P | Mike | Grace | MLB |
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| 30 | 8 | 704 | 1995 | Inaugural Draft | P | Rene | Arocha | MLB |
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| 31 | 17 | 737 | 1995 | Inaugural Draft | OF | Marc | Newfield | MLB |
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| 32 | 8 | 752 | 1995 | Inaugural Draft | 2B | Geronimo | Pena | MLB |
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| 33 | 17 | 785 | 1995 | Inaugural Draft | C | Joe | Siddall | MLB |
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| 34 | 8 | 800 | 1995 | Inaugural Draft | C+ | Barry | Lyons | MLB |
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| 35 | 17 | 833 | 1995 | Inaugural Draft | 1B+ | Dan | Masteller | MLB |
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| 36 | 8 | 848 | 1995 | Inaugural Draft | P | Frank | Rodriguez | MLB |
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| 37 | 17 | 881 | 1995 | Inaugural Draft | OF | Jose | Herrera | MLB |
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| 38 | 8 | 896 | 1995 | Inaugural Draft | P | John | Farrell | MLB |
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| 39 | 17 | 929 | 1995 | Inaugural Draft | 2B | John | Patterson | MLB |
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| 40 | 8 | 944 | 1995 | Inaugural Draft | P | Dave | Swartzbaugh | MLB |
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