| 1101 | 20:52.30 | Jerek | Shoemaker | 33 | 2009-09-05 | 2009 Manhattan Invitational |
| 1102 | 20:52.68 | Jack | Polley | 25 | 2010-10-16 | 2010 AVCTL XC Championships |
| 1103 | 20:53.60 | Kadin | McBee | 59 | 2016-10-08 | 2016 El Dorado Invitational |
| 1104 | 20:54.00 | Andrew | Gehring | 52 | 2011-09-15 | 2011 Buhler Invitational |
| 1105 | 20:54.20 | Creed | Ekerberg | 20 | 2017-08-30 | 2017 Hesston Swather Special |
| 1106 | 20:54.70 | Creed | Ekerberg | 5 | 2017-09-13 | 2017 Buhler Invitational |
| 1107 | 20:55 | Angus | Siemens | 21 | 2012-10-07 | 2012 El Dorado Invitational |
| 1108 | 20:55.40 | Jakob | Senn | 40 | 2019-10-05 | 2019 Newton Invitational |
| 1109 | 20:55.90 | Nicholas | Treaster | 41 | 2019-10-05 | 2019 Newton Invitational |
| 1110 | 20:56.62 | Joseph | Kondziola | 14 | 2009-10-17 | 2009 AVCTL Championships - Lake Afton |
| 1111 | 20:57.24 | Kendall | Gaeddert | 40 | 2012-09-01 | 2012 Manhattan Invitational |
| 1112 | 20:57.72 | Dalton | Schwab | 43 | 2013-09-13 | 2013 Hesston Swather Special |
| 1113 | 20:58.00 | Andre | Rocha | 44 | 2012-09-06 | 2012 Hesston Swather Special |
| 1114 | 20:58.00 | Jorge | Medina | 52 | 2014-09-07 | 2014 Manhattan Invitational |
| 1115 | 20:59.00 | Gabe | Torres | 51 | 2011-09-03 | 2011 Manhattan Invitational |
| 1116 | 20:59.65 | Zach | Stanley | 27 | 2009-09-10 | 2009 Hesston Swather Special |
| 1117 | 21:00.00 | Adam | Wagner | 42 | 2007-09-20 | 2007 McPherson Invitational |
| 1118 | 21:00.10 | Conner | Ekerberg | 28 | 2015-09-06 | 2015 Manhattan Invitational |
| 1119 | 21:00.55 | Ben | Crawford | 36 | 2019-10-19 | 2019 AVCTL Div. 1 Championships |
| 1120 | 21:01.83 | Cory | Helsper | 57 | 2010-10-02 | 2010 Newton Invitational |
| 1121 | 21:02.70 | Conner | Ekerberg | 5 | 2014-09-19 | 2014 Buhler Invitational |
| 1122 | 21:02.80 | Justice | Grant | 12 | 2013-09-20 | 2013 Buhler Invitational |
| 1123 | 21:03.0 | Kadin | McBee | 36 | 2016-09-08 | 2016 Hesston Swather Special |
| 1124 | 21:03.71 | Jonah | Wagner | 9 | 2011-09-22 | 2011 McPherson Invitational |
| 1125 | 21:04.00 | Dylan | Koerner | 59 | 2007-10-06 | 2007 El Dorado Invitational |
| 1126 | 21:04.54 | Gabe | Torres | 39 | 2011-09-22 | 2011 McPherson Invitational |
| 1127 | 21:04.80 | Ben | Crawford | 39 | 2019-09-26 | 2019 Goddard Invitational |
| 1128 | 21:04.96 | Alex | Navarro | 22 | 2006-09-21 | 2006 McPherson Invitational |
| 1129 | 21:05.10 | Angus | Siemens | 6 | 2014-09-19 | 2014 Buhler Invitational |
| 1130 | 21:05.28 | Elijah | Edwards | 56 | 2017-10-03 | 2017 El Dorado Invitational |
| 1131 | 21:05.60 | Creed | Ekerberg | 29 | 2018-09-01 | 2018 Manhattan Invitational |
| 1132 | 21:06.00 | Jack | Polley | 53 | 2011-09-03 | 2011 Manhattan Invitational |
| 1133 | 21:06.80 | Oscar | Gonzalez | 27 | 2014-10-19 | 2014 AVCTL XC Championships - Lake Afton |
| 1134 | 21:07.36 | Jack | Polley | 41 | 2011-09-22 | 2011 McPherson Invitational |
| 1135 | 21:07.90 | Nicholas | Treaster | 43 | 2019-09-26 | 2019 Goddard Invitational |
| 1136 | 21:09.16 | Cody | Mick | 33 | 2009-09-10 | 2009 Hesston Swather Special |
| 1137 | 21:09.2 | Spencer | Steinmetz | 18 | 2019-09-12 | 2019 Hesston Swather Special |
| 1138 | 21:10.00 | Rene' | Madrigal | 33 | 2007-09-29 | 2007 Newton Invitational |
| 1139 | 21:10.70 | Elijah | Edwards | 6 | 2017-09-13 | 2017 Buhler Invitational |
| 1140 | 21:11.1 | Justin | Franz | 17 | 2019-09-12 | 2019 Hesston Swather Special |
| 1141 | 21:11.41 | Jason | Catache | 59 | 2017-10-03 | 2017 El Dorado Invitational |
| 1142 | 21:11.70 | Luca | Lomonaco | 62 | 2011-09-15 | 2011 Buhler Invitational |
| 1143 | 21:12.00 | Jacob | Beebe | 13 | 2008-09-11 | 2008 Hesston Swather Special |
| 1144 | 21:12.27 | Brennan | Miller | 64 | 2010-10-02 | 2010 Newton Invitational |
| 1145 | 21:12.38 | Pablo | Llamas | 88 | 2009-10-10 | 2009 El Dorado Invitational |
| 1146 | 21:12.4 | Elijah | Edwards | 22 | 2019-09-19 | 2019 Hays Invitational |
| 1147 | 21:12.60 | Elijah | Edwards | 10 | 2018-09-13 | 2018 Buhler Invitational |
| 1148 | 21:12.60 | Conner | Ekerberg | 8 | 2015-09-17 | 2015 Buhler Invitational |
| 1149 | 21:12.91 | Zach | Stanley | 89 | 2009-10-10 | 2009 El Dorado Invitational |
| 1150 | 21:13.00 | Jacob | Beebe | 44 | 2009-10-03 | 2009 Newton Invitational |