| 500 FREE | ||||||
| RK | SWIMMER | TEAM | GR | 1998-1999 | 1999-2000 | BEST |
| 1 | THOMPSON, DUSTIN | MUNSTER | 11 | 4:34.95 | 4:48.41 | 4:34.95 |
| 2 | AMES, CHAD | CRAWFORDSVILLE | 10 | 4:36.39 | 4:39.66 | 4:36.39 |
| 3 | HUNTER, LOGAN | BLOOMINGTON SOUTH | 12 | 4:36.40 | 4:47.33 | 4:36.40 |
| 4 | HARTLEY, BRIAN | NORTH CENTRAL | 10 | 4:40.64 | 4:37.96 | 4:37.96 |
| 5 | FLAMION, CHRIS | PLAINFIELD | 11 | 4:40.25 | 4:39.58 | 4:39.58 |
| 6 | PESSAGNO, PETER | CARMEL | 11 | 4:40.76 | 4:45.13 | 4:40.76 |
| 7 | RICHEY, CHRIS | FRANKLIN CENTRAL | 12 | 4:44.40 | 4:46.48 | 4:44.40 |
| 8 | ELLIS, KYLE | PLAINFIELD | 11 | 4:44.47 | 4:44.47 | |
| 9 | HUNT, BRYCE | CASTLE | 12 | 4:44.91 | 4:44.91 | |
| 10 | HESTER, MATT | LAFAYETTE JEFFERSON | 12 | 4:45.63 | 4:48.96 | 4:45.63 |
| 11 | BRINGMAN, GARTH | COLUMBUS NORTH | 12 | 4:47.86 | 4:49.09 | 4:47.86 |
| 12 | BOUNDS, RYAN | CONCORD | 12 | 4:48.04 | 4:59.08 | 4:48.04 |
| 13 | LEHMAN, IAN | MACONAQUAH | 12 | 4:48.28 | 4:48.28 | |
| 14 | BARRY, SETH | CHESTERTON | 10 | 4:48.43 | 4:51.06 | 4:48.43 |
| 15 | BEHRLE, KEVIN | CARMEL | 10 | 4:49.71 | 5:04.66 | 4:49.71 |
| 16 | YOUNG, ANDY | CENTER GROVE | 12 | 4:51.11 | 4:51.11 | |
| 17 | DAWSON, ALEX | NORTH CENTRAL | 10 | 4:51.39 | 4:51.39 | |
| 18 | ECKSTEIN, JAMEY | LAKE CENTRAL | 10 | 4:52.40 | 4:54.92 | 4:52.40 |
| 19 | HAWLEY, ISAAC | MT. VERNON | 12 | 4:52.86 | 4:55.20 | 4:52.86 |
| 20 | BIBERSTINE, ZACHARY | NORWELL | 11 | 4:53.03 | 4:53.03 | |
| 21 | ALLEN, DANIEL | MT. VERNON | 11 | 4:53.50 | 4:57.72 | 4:53.50 |
| 22 | EICHELMAN, NICK | CENTER GROVE | 9 | 4:53.68 | 4:53.68 | |
| 23 | LUTKUS, JAMIE | PENN | 10 | 4:53.90 | 4:53.90 | |
| 24 | RODECKER, MIKE | HAMILTON SOUTHEASTERN | 12 | 4:54.90 | 4:56.21 | 4:54.90 |
| 25 | RANDOLPH, TIMOTHY | MERRILLVILLE | 10 | 4:55.13 | 4:55.13 | |
| 26 | PHIPPS, CHRISTIAN | CARMEL | 9 | 4:55.24 | 4:55.24 | |
| 27 | HITCHENS, CHASE | CARMEL | 4:55.52 | 4:55.52 | ||
| 28 | BOWMAN, RYAN | DELTA | 11 | 4:55.68 | 4:55.68 | |
| 29 | BEALL, BRIAN | BREMEN | 12 | 4:55.74 | 4:55.74 | |
| 30 | ENOCH, MARK | CARMEL | 9 | 4:56.11 | 4:56.11 | |
| 31 | LEAR, KURTIS | EAST NOBLE | 10 | 4:56.97 | 4:56.61 | 4:56.61 |
| 32 | CLEAVER, JESSIE | HUNTINGTON NORTH | 9 | 4:58.01 | 4:58.01 | |