| Long Jump |
|
| Penn Record |
| Year | Champion | School | Mark |
| 2024 | Balvin Israel | Jamaica College, JAM | 23-9 |
| 2023 | Demario Prince | St. Jago, JAM | 24-4.25 |
| 2022 | Gregory Foster | Lawrenceville Sch., NJ | 24-11 |
| 2019 | Wayne Pinnock | Kingston College, JAM | 25-10 |
| 2018 | Wayne Pinnock | Kingston College, JAM | 25-10.25 |
| 2017 | William Henderson | Baltimore Tech, MD | 25-2.25 |
| 2016 | Rayvon Grey | Beacon, NY | 25-2.25 |
| 2015 | Jullanie Walker | Calabar, JAM | 24-5 |
| 2014 | Dashawn Taylor | Longwood, NY | 23-6.25 |
| 2013 | Sadiki Eddie | Calabar, JAM | 23-10.75 |
| 2012 | Clive Pullen | Kingston College, JAM | 24-2.75 |
| 2011 | Jerome Wilson | Kingston College, JAM | 24-3.75 |
| 2010 | Kamal Fuller | Wolmer's, JAM | 24-10 |
| 2009 | Carlton Lavong | Methacton, PA | 24-6½ |
| 2008 | James Taylor | Nansemond River, VA | 23-10.75 |
| 2007 | Tarik Batchelor | Kingston College, JAM | 24-11.75 |
| 2006 | Alain Bailey | Kingston College, JAM | 24-5.75 |
| 2005 | Larrone Moore | Northwestern, MD | 23-4.75 |
| 2004 | Dennis Boone | Thomas Dale, VA | 23-6.25 |
| 2003 | Anthony Miles | Winslow Twp, NJ | 24-6 |
| 2002 | Will Nunez | Washingtonville, NY | 22-5 |
| 2001 | I-Perfection Harris | Poly Prep, NY | 24-1.75 |
| 2000 | Aundre Edwards | Wolmer's, JAM | 24-11 |
| 1999 | Aundre Edwards | Wolmer's, JAM | 23-11 |
| 1998 | Kai Maull | Cape Henlopen, DE | 24-9 |
| 1997 | Chauncey Rogers | Denbigh, VA | 23-9.5 |
| 1996 | William Spearman | Wilson, NJ | 23-10.75 |
| 1995 | Maurice Wingall | Calabar, JAM | 24-6.25 |
| 1994 | Maurice Wingall | Calabar, JAM | 25-2.75 |