Bobby Ray Matthews, age 80, passed away Thursday, May 21, 2026 at Harmony at Oakbrooke, Chesapeake, VA.

He was born shortly after the end of World War II on October 7, 1945 in Tarboro, North Caroline to James and Fannie Matthews.

Bobby grew to become a loving son, father, grandfather, and friend. He was a proud veteran having served our country honorably in the United States Army during the Vietnam Era. He retired as a Training Director for Mears Transportation in Orlando, Florida. He enjoyed his Harley Davidson and exploring.

Bobby made a lasting impact on many lives, especially for those who will miss him most: his children Angela Ryan (Jim), Pamela Whitfield (Fred), and Robert Matthews; grandchildren Ashley Sikes (Josh), Samantha Whitfield, Madison Whitfield, Makayla Whitfield, and Christopher Whitfield; great-grandchildren, Wesley, Paisley, Savannah, Jed, and Noah. He also leaves his siblings, Delories Overstreet, Gloria Smith, and Jay Matthews.

A private family gathering to celebrate Bobby will be held at a later date.