| 100 FLY | ||||||
| RK | SWIMMER | TEAM | GR | 1998-1999 | 1999-2000 | BEST |
| 1 | MCDONALD, MATT | HAMILTON SOUTHEASTERN | 11 | 49.26 | 50.61 | 49.26 |
| 2 | SHEEHY, ALEC | COLUMBUS NORTH | 12 | 49.60 | 52.18 | 49.60 |
| 3 | AMES, CHAD | CRAWFORDSVILLE | 10 | 51.15 | 51.15 | |
| 4 | SUTTON, BENJAMIN | FORT WAYNE CONCORDIA | 12 | 51.27 | 53.00 | 51.27 |
| 5 | SHAW, JONATHAN | CASTLE | 12 | 51.74 | 51.74 | |
| 6 | YOUNG, ANDY | CENTER GROVE | 12 | 52.17 | 52.00 | 52.00 |
| 7 | FROBESE, ANDREAS | LAPORTE | 11 | 52.95 | 52.75 | 52.75 |
| 8 | HUNT, BRYCE | CASTLE | 12 | 52.98 | 52.98 | |
| 9 | BIRD, PATRICK | DELTA | 11 | 53.01 | 53.01 | |
| 10 | HOUSER, JARAD | KOKOMO | 12 | 53.46 | 54.85 | 53.46 |
| 11 | EATON, BRIAN | MT. VERNON | 10 | 53.57 | 54.19 | 53.57 |
| 12 | LAPINSKAS, JOE | WEST LAFAYETTE | 12 | 53.65 | 53.65 | |
| 13 | HAGEMAN, JOEL | HOMESTEAD | 12 | 53.66 | 53.66 | |
| 14 | HELFRICH, ADAM | WARSAW | 55.18 | 55.18 | ||
| 15 | O'HERAN, ROB | BLOOMINGTON NORTH | 12 | 53.82 | 56.70 | 53.82 |
| 16 | MARTIN, CHRIS | NORTH CENTRAL | 11 | 54.16 | 53.91 | 53.91 |
| 17 | BOWMAN, RYAN | DELTA | 11 | 53.96 | 53.96 | |
| 18 | HALL, ZACH | CHESTERTON | 11 | 54.07 | 54.10 | 54.07 |
| 19 | THOMPSON, DUSTIN | MUNSTER | 11 | 54.09 | 54.09 | |
| 20 | ELLIS, KYLE | PLAINFIELD | 11 | 54.11 | 54.11 | |
| 21 | DRAPER, CORY | NORTHRIDGE | 12 | 54.29 | 56.21 | 54.29 |
| 22 | FLAMION, CHRIS | PLAINFIELD | 11 | 54.35 | 54.35 | |
| 23 | PEACOCK, BRANDON | CRAWFORDSVILLE | 12 | 54.40 | 55.08 | 54.40 |
| 24 | MALLORY, KYLE | PENN | 11 | :54.49 | 54.49 | |
| 25 | FOX, JOE | FLOYD CENTRAL | 10 | 54.87 | 54.51 | 54.51 |
| 26 | HEWITT, MICHAEL | CENTER GROVE | 9 | 54.75 | 54.75 | |
| 27 | MULLALLY, ROB | RICHMOND | 12 | 54.76 | 55.01 | 54.76 |
| 28 | RECTOR, BRANDON | CARMEL | 9 | 54.78 | 54.78 | |
| 29 | RODECKER, BRAD | HAMILTON SOUTHEASTERN | 12 | 54.80 | 56.84 | 54.80 |
| 30 | RECTOR, JOEL | FORT WAYNE CONCORDIA | 11 | 54.82 | 56.84 | 54.82 |
| 31 | CLEVENGER, ANDY | YORKTOWN | 12 | 55.01 | 57.06 | 55.01 |
| 32 | DEXTER, BEN | RONCALLI | 10 | 55.26 | 55.26 | |