| Rank | Name | Active | Year | Meet | Time |
|---|---|---|---|---|---|
| 01 | Josh Rodgers | 2017 | Naperville Twilight | 14:36.6 | |
| 02 | Andrew Nelson | 2008 | State | 14:41.2 | |
| 03 | Kevin McDowell | 2008 | State | 14:46.5 | |
| 04 | Ryan Kredell | 2018 | State | 14:48.33 | |
| 05 | Chris Higgins | 2008 | State | 14:54.4 | |
| 06 | Tyler Dau | 2016 | State | 14:54.81 | |
| 07 | Andrew McQuillan | 2000 | Regional | 14:55.2 | |
| 08 | Justin Mitchell | 1997 | State | 14:55.5 | |
| 09 | Dan Huling | 2000 | Regional | 14:55.7 | |
| 10T | Billy Koskiewicz | 2010 | State | 14:58.0 | |
| 10T | Kevin Sparks | 2009 | State | 14:58.0 | |
| 12 | Greg Adelman | 2008 | State | 14:59.7 | |
| 13 | Matt Saarima | 1996 | State | 15:00.0 | |
| 14 | Mitchael Deamantopulos | 2014 | Sectional | 15:01.0 | |
| 15 | Ben Calusinski | 2018 | State | 15:03.53 | |
| 16 | Mike Bianchina | 2012 | Sectional | 15:13.8 | |
| 17 | Blaine Bartel | 2013 | Conference | 15:17.3 | |
| 18 | Kellen Cesarone | 2018 | State | 15:19.29 | |
| 19 | Brian Kuehl | 2016 | State | 15:22.88 | |
| 20T | Matt Bowman | 2006 | Regional | 15:25.0 | |
| 20T | Peter Archibald | 2010 | State | 15:25.0 | |
| 22T | Andrew Isbell | 2006 | State | 15:28.0 | |
| 22T | Charlie Connor | 1999 | State | 15:28.0 | |
| 24 | Dan Herrera | 2012 | Sectional | 15:28.7 | |
| 25 | Evan Ehrhardt | 2007 | Woodruff | 15:30.0 | |
| 26 | Craig Young | 2000 | Regional | 15:33.0 | |
| 27 | Dave Rauch | 2000 | Regional | 15:34.0 | |
| 28 | Julian Hipp | Yes | 2023 | Sectional | 15:36.7 |
| 29 | Connor Bartel | 2010 | State | 15:40.0 | |
| 30 | Brian Caskey | 2015 | Peoria ND | 15:41.4 | |
| 31 | Jordan Midgley | 2012 | Conference | 15:41.8 | |
| 32 | Mike Aitken | 2002 | STC East | 15:42.0 | |
| 33T | Conor Sparks | 2005 | Regional | 15:43.0 | |
| 33T | Ryan Ahern | 2010 | State | 15:43.0 | |
| 35 | Cole Montgomery | 2017 | State | 15:43.05 | |
| 36 | Jake Tracey | 2014 | Sectional | 15:43.4 | |
| 37 | Boon Andrews | 2015 | NS/SS Challenge | 15:44 | |
| 38 | Nathan Lehman | 2021 | Regional | 15:45.1 | |
| 39 | Drew Hickey | 2008 | State | 15:46.9 | |
| 40 | Valdis Slokenbergs | 2018 | Richard Spring | 15:47.3 | |
| 41 | Dominic Ross | Yes | 2024 | Naperville Twilight | 15:47.51 |
| 42 | Nate Wendt | 2012 | Conference | 15:47.6 | |
| 43 | Brian Honeyman | 2001 | State | 15:51.0 | |
| 44 | Andrew Warcup | 2022 | Sterling | 15:51.4 | |
| 45 | Ryan Rasmussen | 2012 | North Stars Invite | 15:52.0 | |
| 46T | Jeff Noethlich | 2001 | State | 15:53.0 | |
| 46T | Justin Rodriguez | 2009 | State | 15:53.0 | |
| 48 | Matt Hoskins | 2017 | State | 15:54.14 | |
| 49 | Colby Coronado | 2020 | Sectional | 15:55:80 | |
| 50 | Scott Creger | 2016 | State | 15:57.55 | |
| 51 | Steve Jeske | 2000 | Regional | 15:58.0 | |
| 52 | Anthony Ross | 2022 | Conference | 15:58.2 | |
| 53 | Noah Martin | Yes | 2024 | Naperville Twilight | 15:59.86 |
Note: Records and times prior to 1995 are not available so there might be some question of accuracy. If missing records become available and other individuals belong among this sub 16:00, the chart will be adjusted accordingly.