The Lancaster-Lebanon League Sportsmanship Award was created in the 1999-2000 school year to recognize the member school(s) that exemplify the quality of sportsmanship throughout each sport season and throughout the school year.
| Year | Fall | Winter | Spring | Overall |
| 2015-2016 | Solanco | Elizabethtown | Conestoga Valley | Solanco |
| 2014-2015 | Solanco | Garden Spot | Warwick | Warwick |
| 2013-2014 | McCaskey | Manheim Central | Lampeter Strasburg | Lampeter Strasburg |
| 2012-2013 | Solanco | Warwick | Lancaster Mennonite | Warwick |
| 2011-2012 | Cocalico | Donegal | Lancaster Mennonite | Cocalico |
| 2010-2011 | Solanco | McCaskey | Lampeter Strasburg | Lampeter Strasburg |
| 2009-2010 | Warwick | Pequea Valley | Annville-Cleona | Annville-Cleona |
| 2008-2009 | Warwick | Penn Manor | Annville-Cleona | Penn Manor |
| 2007-2008 | Lampeter Strasburg | McCaskey | Penn Manor | Lampeter Strasburg |
| 2006-2007 | Annville-Cleona | Cocalico | Cocalico | Cocalico |
| 2005-2006 | McCaskey | Cedar Crest | Lampeter Strasburg | Lampeter Strasburg |
| 2004-2005 | Warwick | Garden Spot | Lampeter Strasburg | Lancaster Mennonite |
| 2003-2004 | Cocalico | ELCO | McCaskey | Cocalico |
| 2002-2003 | Garden Spot | Pequea Valley | Garden Spot | |
| 2001-2002 | Lancaster Mennonite | Pequea Valley | Warwick | Warwick |
| 2000-2001 | Annville-Cleona | Lancaster Mennonite | McCaskey | McCaskey |
| 1999-2000 | McCaskey | Warwick | Penn Manor | McCaskey |