| Gabe Blake (Sr.) | Delta Invitational | Gold Varsity | 7 | 17:29.80 |
| Skyler Schrope (So.) | Delta Invitational | Gold Varsity | 10 | 17:43.30 |
| Gabe Blake (Sr.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 24 | 17:49.00 |
| Skyler Schrope (So.) | Marion Invitational | Gold Division | 26 | 17:49.80 |
| Skyler Schrope (So.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 28 | 17:54.00 |
| Will Huffman (Jr.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 30 | 17:55.00 |
| Gabe Blake (Sr.) | Centerville Invitational | | 2 | 17:59.80 |
| Will Huffman (Jr.) | Marion Invitational | Gold Division | 30 | 18:01.20 |
| Will Huffman (Jr.) | Delta Invitational | Gold Varsity | 19 | 18:04.80 |
| Gabe Blake (Sr.) | Eastern Hancock Invitational | | 4 | 18:06.00 |
| Skyler Schrope (So.) | Centerville Invitational | | 4 | 18:15.00 |
| Gabe Blake (Sr.) | Rushville Invitational | Boys Division II | 11 | 18:15.85 |
| Gabe Blake (Sr.) | Marion Invitational | Gold Division | 34 | 18:17.00 |
| Gabe Blake (Sr.) | Triton Central Invitational | Triton Central Early Bird | 18 | 18:22.92 |
| Skyler Schrope (So.) | Eastern Hancock Invitational | | 5 | 18:24.00 |
| Skyler Schrope (So.) | Triton Central Invitational | Triton Central Early Bird | 19 | 18:25.20 |
| Skyler Schrope (So.) | Rushville Invitational | Boys Division II | 15 | 18:25.31 |
| Gabe Blake (Sr.) | Hancock County Meet | | 12 | 18:27.22 |
| Gabe Blake (Sr.) | Meister Family Memorial Run | Varsity Boys | 29 | 18:27.40 |
| Will Huffman (Jr.) | Eastern Hancock Invitational | | 6 | 18:32.00 |
| Skyler Schrope (So.) | Meister Family Memorial Run | Varsity Boys | 31 | 18:35.40 |
| Will Huffman (Jr.) | Meister Family Memorial Run | Varsity Boys | 33 | 18:36.80 |
| Skyler Schrope (So.) | Hancock County Meet | | 14 | 18:39.04 |
| Will Huffman (Jr.) | Rushville Invitational | Boys Division II | 22 | 18:39.78 |
| Gabe Blake (Sr.) | Blackford Invitational | | 16 | 18:54.60 |
| Will Huffman (Jr.) | Triton Central Invitational | Triton Central Early Bird | 31 | 18:55.03 |
| Alvaro Cosmen Valero (Jr.) | Delta Invitational | Gold Varsity | 40 | 18:59.00 |
| Will Huffman (Jr.) | Hancock County Meet | | 27 | 19:21.18 |
| Skyler Schrope (So.) | Blackford Invitational | | 26 | 19:22.40 |
| Alvaro Cosmen Valero (Jr.) | Eastern Hancock Invitational | | 13 | 19:32.00 |
| Nick Edwards (Fr.) | Delta Invitational | Gold Varsity | 49 | 19:33.10 |
| Alvaro Cosmen Valero (Jr.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 50 | 19:34.00 |
| Alvaro Cosmen Valero (Jr.) | Marion Invitational | Gold Division | 71 | 19:35.10 |
| Nick Edwards (Fr.) | Marion Invitational | Gold Division | 73 | 19:37.30 |
| Will Huffman (Jr.) | Centerville Invitational | | 14 | 19:45.60 |
| Alvaro Cosmen Valero (Jr.) | Centerville Invitational | | 15 | 19:47.30 |
| Nick Edwards (Fr.) | Eastern Hancock Invitational | | 15 | 19:48.00 |
| Nick Edwards (Fr.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 53 | 19:50.00 |
| Nick Edwards (Fr.) | Centerville Invitational | | 16 | 19:54.00 |
| Alvaro Cosmen Valero (Jr.) | Rushville Invitational | Boys Division II | 53 | 20:01.70 |
| Alvaro Cosmen Valero (Jr.) | Hancock County Meet | | 34 | 20:10.27 |
| Nick Edwards (Fr.) | Meister Family Memorial Run | Varsity Boys | 83 | 20:15.20 |
| Alvaro Cosmen Valero (Jr.) | Meister Family Memorial Run | Varsity Boys | 86 | 20:17.60 |
| Nick Edwards (Fr.) | Hancock County Meet | | 36 | 20:21.16 |
| Nick Edwards (Fr.) | Rushville Invitational | Boys Division II | 68 | 20:41.75 |
| Will Huffman (Jr.) | Blackford Invitational | | 65 | 20:50.10 |
| Zach Sickle (So.) | Delta Invitational | Gold Varsity | 67 | 21:07.60 |
| Zach Sickle (So.) | Marion Invitational | Gold Division | 136 | 21:08.10 |
| Alvaro Cosmen Valero (Jr.) | Blackford Invitational | | 71 | 21:08.50 |
| Zach Sickle (So.) | Centerville Invitational | | 36 | 22:04.00 |
| Nick Edwards (Fr.) | Blackford Invitational | | 94 | 22:10.10 |
| Zach Sickle (So.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 64 | 22:17.00 |
| Zach Sickle (So.) | Eastern Hancock Invitational | | 35 | 22:54.00 |
| Zach Sickle (So.) | Meister Family Memorial Run | Varsity Boys | 158 | 22:56.80 |
| Zach Sickle (So.) | Rushville Invitational | Boys Division II | 105 | 23:14.98 |
| Zach Sickle (So.) | Hancock County Meet | | 62 | 23:21.23 |
| Kyle Moore (So.) | Delta Invitational | Gold Varsity | 89 | 23:50.60 |
| Zach Sickle (So.) | Blackford Invitational | | 123 | 23:52.40 |
| Kyle Moore (So.) | Eastern Hancock Invitational | | 38 | 23:54.00 |
| Kyle Moore (So.) | Marion Invitational | Gold Division | 182 | 24:22.90 |
| Kyle Moore (So.) | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 2016 IHSAA New Palestine Sectional Boys Cross Country Meet | 67 | 24:23.00 |
| Zach Sickle (So.) | Triton Central Invitational | Triton Central Early Bird | 119 | 24:37.01 |
| Kyle Moore (So.) | Hancock County Meet | | 67 | 25:24.25 |
| Kyle Moore (So.) | Centerville Invitational | | 49 | 25:46.40 |
| Kyle Moore (So.) | Meister Family Memorial Run | Varsity Boys | 205 | 26:45.10 |
| Kyle Moore (So.) | Blackford Invitational | | 161 | 26:52.40 |
| Kyle Moore (So.) | Rushville Invitational | Boys Division II | 119 | 27:54.09 |
| Kyle Moore (So.) | Triton Central Invitational | Triton Central Early Bird | 135 | 27:56.15 |
