Orlando Sentinel
“Varsity Cup” All Sports Award
Total Awards — 13
| Year | Place | Year | Place |
| 2018 – 2019 | 2nd | 2008 – 2009 | 1st |
| 2017 – 2018 | 1st | 2007 – 2008 | 1st |
| 2016 – 2017 | 1st | 2006 – 2007 | 1st |
| 2015 – 2016 | 1st | 2005 – 2006 | 1st |
| 2014 – 2015 | 2nd | 2004 – 2005 | 2nd |
| 2013 – 2014 | 1st | 2003 – 2004 | 1st |
| 2012 – 2013 | 4th | 2002 – 2003 | 2nd |
| 2011 – 2012 | 1st | 2001 – 2002 | 2nd |
| 2010 – 2011 | 2nd | 2000 – 2001 | 1st |
| 2009 – 2010 | 1st | 1999 – 2000 | 1st |
| Other Winners | |||
| 2001 – 2002 | Lake Highland Prep | ||
| 2002 – 2003 | Oviedo HS | ||
| 2004 – 2005 | Lake Mary HS | ||
| 2010 – 2011 | Dr. Phillips HS | ||
| 2012 – 2013 | Dr. Phillips HS | ||
| 2014 – 2015 | Lake Highland Prep | ||
| 2018 – 2019 | Oviedo HS | ||
| Total number of awards | |||
| Winter Park HS | 13 | ||
| Dr. Phillips HS | 2 | ||
| Lake Highland Prep | 2 | ||
| Oviedo HS | 2 | ||
| Lake Mary HS | 1 | ||
This award is presented by the Orlando Sentinel to the top athletic program in Central Florida (approx. 90 high schools) based on regular season and post season success.