| 1051 | 20:46.29 | Jerek | Shoemaker | 24 | 2009-09-10 | 2009 Hesston Swather Special |
| 1052 | 20:46.8 | Kenton | Fox | 11 | 2016-09-15 | 2016 Buhler Invitational |
| 1053 | 20:47.00 | Shawn | Lettau | 32 | 2014-09-12 | 2014 Hesston Swather Special |
| 1054 | 20:47.90 | Nathan | Boyles | 27 | 2010-09-09 | 2010 Hesston Swather Special |
| 1055 | 20:47.91 | Nathan | Boyles | 42 | 2010-09-04 | 2010 Manhattan Invitational |
| 1056 | 20:48.40 | Konner | Jaso | 2 | 2018-09-29 | 2018 Newton Invitational |
| 1057 | 20:48.60 | Clayton | Kaufman | 38 | 2019-10-05 | 2019 Newton Invitational |
| 1058 | 20:48.60 | Kenton | Fox | 53 | 2016-09-03 | 2016 Manhattan Invitational |
| 1059 | 20:48.75 | Keagan | Attebery | 27 | 2009-09-10 | 2009 Hesston Swather Special |
| 1060 | 20:48.94 | Nate | Troyer | 68 | 2006-09-02 | 2006 Manhattan Invitational |
| 1061 | 20:49.00 | Alex | Navarro | 40 | 2007-09-20 | 2007 McPherson Invitational |
| 1062 | 20:49.73 | Andrew | Gehring | 37 | 2011-10-15 | 2011 AVCTL XC Championships - Derby |
| 1063 | 20:49.81 | Jacob | Beebe | 84 | 2009-10-10 | 2009 El Dorado Invitational |
| 1064 | 20:50.00 | Dylan | Koerner | 32 | 2008-09-25 | 2008 McPherson Invitational |
| 1065 | 20:50.00 | Jonah | Hodge | 3 | 2015-09-17 | 2015 Buhler Invitational |
| 1066 | 20:50.50 | Grant | Treaster | 6 | 2018-09-13 | 2018 Buhler Invitational |
| 1067 | 20:50.56 | Andrew | Gehring | 13 | 2011-10-08 | 2011 El Dorado Invitational |
| 1068 | 20:51.10 | Caleb | Nelson | 8 | 2013-09-20 | 2013 Buhler Invitational |
| 1069 | 20:51.60 | Conner | Ekerberg | 9 | 2013-09-20 | 2013 Buhler Invitational |
| 1070 | 20:51.60 | Alexander | Barnett | 29 | 2018-09-06 | 2018 Hesston Swather Special |
| 1071 | 20:52.30 | Jerek | Shoemaker | 33 | 2009-09-05 | 2009 Manhattan Invitational |
| 1072 | 20:52.68 | Jack | Polley | 25 | 2010-10-16 | 2010 AVCTL XC Championships |
| 1073 | 20:53.60 | Kadin | McBee | 59 | 2016-10-08 | 2016 El Dorado Invitational |
| 1074 | 20:54.00 | Andrew | Gehring | 52 | 2011-09-15 | 2011 Buhler Invitational |
| 1075 | 20:54.20 | Creed | Ekerberg | 20 | 2017-08-30 | 2017 Hesston Swather Special |
| 1076 | 20:54.70 | Creed | Ekerberg | 5 | 2017-09-13 | 2017 Buhler Invitational |
| 1077 | 20:55 | Angus | Siemens | 21 | 2012-10-07 | 2012 El Dorado Invitational |
| 1078 | 20:55.40 | Jakob | Senn | 40 | 2019-10-05 | 2019 Newton Invitational |
| 1079 | 20:55.90 | Nicholas | Treaster | 41 | 2019-10-05 | 2019 Newton Invitational |
| 1080 | 20:56.62 | Joseph | Kondziola | 14 | 2009-10-17 | 2009 AVCTL Championships - Lake Afton |
| 1081 | 20:57.24 | Kendall | Gaeddert | 40 | 2012-09-01 | 2012 Manhattan Invitational |
| 1082 | 20:57.72 | Dalton | Schwab | 43 | 2013-09-13 | 2013 Hesston Swather Special |
| 1083 | 20:58.00 | Andre | Rocha | 44 | 2012-09-06 | 2012 Hesston Swather Special |
| 1084 | 20:58.00 | Jorge | Medina | 52 | 2014-09-07 | 2014 Manhattan Invitational |
| 1085 | 20:59.00 | Gabe | Torres | 51 | 2011-09-03 | 2011 Manhattan Invitational |
| 1086 | 20:59.65 | Zach | Stanley | 27 | 2009-09-10 | 2009 Hesston Swather Special |
| 1087 | 21:00.00 | Adam | Wagner | 42 | 2007-09-20 | 2007 McPherson Invitational |
| 1088 | 21:00.10 | Conner | Ekerberg | 28 | 2015-09-06 | 2015 Manhattan Invitational |
| 1089 | 21:01.83 | Cory | Helsper | 57 | 2010-10-02 | 2010 Newton Invitational |
| 1090 | 21:02.70 | Conner | Ekerberg | 5 | 2014-09-19 | 2014 Buhler Invitational |
| 1091 | 21:02.80 | Justice | Grant | 12 | 2013-09-20 | 2013 Buhler Invitational |
| 1092 | 21:03.0 | Kadin | McBee | 36 | 2016-09-08 | 2016 Hesston Swather Special |
| 1093 | 21:03.71 | Jonah | Wagner | 9 | 2011-09-22 | 2011 McPherson Invitational |
| 1094 | 21:04.00 | Dylan | Koerner | 59 | 2007-10-06 | 2007 El Dorado Invitational |
| 1095 | 21:04.54 | Gabe | Torres | 39 | 2011-09-22 | 2011 McPherson Invitational |
| 1096 | 21:04.80 | Ben | Crawford | 39 | 2019-09-26 | 2019 Goddard Invitational |
| 1097 | 21:04.96 | Alex | Navarro | 22 | 2006-09-21 | 2006 McPherson Invitational |
| 1098 | 21:05.10 | Angus | Siemens | 6 | 2014-09-19 | 2014 Buhler Invitational |
| 1099 | 21:05.28 | Elijah | Edwards | 56 | 2017-10-03 | 2017 El Dorado Invitational |
| 1100 | 21:05.60 | Creed | Ekerberg | 29 | 2018-09-01 | 2018 Manhattan Invitational |