Gregory Scott Cunningham

Gregory S. Cunningham of Winnebago passed away on March 16, 2026, after a challenging battle with dementia. Born October 12, 1951, to Wallace and Margaret Cunningham, Greg graduated from Winnebago High School and served in the Army National Guard. Greg married Juanita Newman on March 16, 1974. He lived his entire life in the Winnebago community and retired from a 40 year career with the Winnebago County Highway Department in 2017.

Greg was a devoted husband, father, and grandfather. He will be remembered by his family as someone who did not hesitate to put the world on hold when they needed him. Greg loved spending time with his grandchildren and never missed a chance to watch them play their favorite sport or participate in an event. He never wavered in his belief in his Savior, Jesus Christ, and was always ready to share His Good News with others. And, as a life-long Chicago Bears fan, the peace God gave him frequently came in handy.

Survived by his wife, Juanita; children, Eric (Ginnie) Cunningham and Todd (Jayme) Cunningham; grandchildren, Haylie, Olivia, Gabriella, and David; brothers, Roger Cunningham, Denny (Sharon) Cunningham, Mike (Ann) Cunningham; and many loving family members. Predeceased by his son, Justin; brother, Bruce Cunningham; and parents, Wallace and Margaret.

Greg's family thanks the staff at Anam Care, Oregon Living and Rehabilitation Center, and Serenity Hospice for their loving care and compassion.

Services will be held at 1:00 PM, Saturday, March 21, 2026, at Park Hills Church, 500 W. Winnebago St., Winnebago, IL 61088, with Pastor Jonathan Pierson officiating. Private burial at Twelve Mile Grove Cemetery, Pecatonica. Visitation 11:00 AM to 1:00 PM, before the service. In lieu of flowers, memorials can be made to the Rockford Rescue Mission, 715 W. State St., Rockford, IL 61102. To share a memory or condolence please visit www.olsonfh.com.