Cynthia T. Simmons Memorial Scholarship Past Recipients
- 1996 – Joy Oliver – Seaford High School – University of Delaware
- 1997 – Kristin Banks – Milford High School – University of Delaware
- 1998 – Willie Savage – Woodbridge High School – University of Delaware
- 1999 – Davita Mumford – Sussex Central High School – University. of Delaware
- 1999 – Ajay Nainani – Cape Henlopen High School –
- 1999 – Christopher Myers – Cape Henlopen High School –
- 2000 – Rachel Valentin – Sussex Tech High School – Spelman College
- 2001 – Ebonie Hughes – Woodbridge High School – Spelman College
- 2002 – Travis Jackson – Seaford High School – Morehouse College
- 2004 – Annalisa Smith – Seaford High School – University of Virginia
- 2005 – Maria Zinser – Laurel High School – University of Delaware
- 2006 – Charisse Holmes – Delmar High School – Wake Forest University
- 2007 – Alan-Michael Hill – Milford High School – University of Pennsylvania
- 2007 – Brittany Terrell – Dover High School – University of Virginia
- 2008 – Jerome Hutson – Woodbridge High School – University of Hawaii
- 2009 – Charesa Smith – Reynolds High School – Harvard University
- 2010 – Rafael Grillo – Parkland High School – Princeton University
- 2011 – Cameron Campbell – Glenn High School – University of North Carolina at Chapel Hill
- 2012 – Paige Woods – Parkland High School – Harvard University
- 2013 – Karina Martinez Romo – Parkland High School – Duke University
- 2013 – Luis Miguel Vasquez – West Forsyth High School – University of North Carolina at Chapel Hill
- 2014 – Semassa Boko – Mount Tabor High School – Pomona College
- 2015 – Marianne Cruzat – Early College of Forsyth – University of North Carolina at Chapel Hill
- 2016 – Caroline Phan – Parkland High School – Davidson College
- 2016 – Andra Woods – Parkland High School – Bowdoin College
- 2016 – Ashley Douglas – Parkland High School – University of Pennsylvania
- 2016 – Maria Cruzat – Early College of Forsyth – UNC Charlotte
- 2017 – Iyon Baker – Early College of Forsyth – UNC Chapel Hill
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2017 – Jada Dove – Glenn High School – UNC Charlotte
- 2018 – Victor Desnoyers – Atkins High School – Howard University
- 2019 – Jayden Brown – Salem Academy – Wake Forest University
- 2020 – Jolie Dumay – Parkland High School – Wake Forest University
- 2021 – Micah Eustache – Parkland Magnet High School – Wellesley College
- 2022 – Dallia Lindell – Parkland Magnet High School – University of North Carolina at Chapel Hill
Nathaniel P. Simmons III Memorial Scholarship Past Recipients
- 2002 – Sylvanna Johnson – Sussex Technical High School – Spelman College
- 2004 – Kimberly Harris – Widener University
- 2005 – Bobby Bowden – Delaware State University
- 2006 – Charis Tomlin – Hampton University
- 2007 – Faith Roach – University of Delaware
- 2008 – Johnathan Charles – University of Delaware
- 2009 – Jordan Showell – Milford High School – Morehouse College
- 2010 – Damaris Ramirez – Parkland High School – Meredith College
- 2011 – Jamie Gorham – Salem Academy – East Carolina University
- 2012 – Britni Wallace – Parkland High School – Oberlin College
- 2013 – Mishana Sturdivant – Robert B Glenn High School – University of North Carolina at Chapel Hill
- 2013 – Ashley Green – Early College Academy at Dudley High School – University of North Carolina at Chapel Hill
- 2014 – Joseph Ford – Parkland High School – Wake Forest University
- 2015 – Jada Baker – Early College of Forsyth – University of North Carolina at Chapel Hill
- 2016 – Jontae Lindsey – East Forsyth High School – UNC Wilmington
- 2016 – Raines Warren – Reynolds High School – Howard University
- 2016 – Alexis Douglas – Parkland High School – NC State University
- 2016 – Jada Moore – Reynolds High School – NC A&T University
- 2016 – Mikalah Muhammad – Atkins High School – NC A&T University
- 2017 – Alese Berry – Reagan High School – Winston Salem State University
- 2018 – Danielle Coan – Early College of Forsyth County- NC State University
- 2019 – Danielle Allen – Atkins High School – North Carolina A&T University
- 2019 – Chigamecha Oparanozie – Parkland High School – North Carolina A&T University
- 2020 – Jaelyn Brown – Reynolds High School – Howard University
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2020 – Nathan Bailey – Atkins High School – North Carolina A&T University
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2021 – Breanna Chadwick – Parkland High School – University of North Carolina at Chapel Hill
- 2021 – Alexis Cooper – Walkertown High School – Elon University
- 2021 – John Jackson – Atkins High School – Mars Hill University
Nathaniel P. Simmons, Jr. Memorial Scholarship Past Recipients
- 2013 – Katerra Logan – Mount Tabor High School – Yale University
- 2013 – Jordan Latham – Parkland High School – University of North Carolina at Chapel Hill
- 2014 – Ebony Watkins – Parkland High School – University of North Carolina at Chapel Hill
- 2015 – Breon Jenkins – West Forsyth High School – Wingate University
- 2015 – Mariah Adams – Walkertown High School – East Carolina University
- 2016 – Roger Cameron Berry – Reagan High School – NC A&T University
- 2017 – Jaylen Jeffries – Reynolds High School – NC A&T University
- 2017 – Jasmine Dove – Glenn High School – UNC Charlotte
- 2018 – Alaina Watkins – Parkland High School – UNC School of the Arts
- 2018 – Kolachi Oparanozie – Parkland High School – George Mason University
- 2019 – Saven Baker – Atkins High School – Morehouse College
- 2020 – Najashi Belcher – Walkertown High School – University of San Francisco
- 2021 – Jackson Brown – Atkins High School – Wake Forest University
- 2022 – Avanish Bharadwaj – Parkland High School – University of North Carolina at Chapel Hill
