

John "Bob" Robert Cunningham Sr., 85, passed away on March 29, 2026. Bob was born in Rural Madison, Indiana to the late, Hugh and Marjorie Cunningham. He joined the United States Navy in 1962, at the age of 20 and served his country faithfully for 20 years. He retired in 1982 as a decorated Chief Petty Officer. Bob loved his church where he was an active member for eighteen years. He loved to sing in the choir, also in groups and play his harmonica and trumpet. Bob liked playing golf with his friends from church and they say he always won.
John is survived by his loving wife of 20 years, Patricia Lou Cunningham; sons: John Robert Cunningham Jr (Kim) - Flagler Beach, FL and Matthew Loyd Cunningham (Marsena)- Madisonville, TN; daughter: Robin Elizabeth Cunningham-Cantwell (Billy) - Aiken, SC; step-daughters: Cathy Gifford - Cincinnati, Ohio and Ladonna Childers (Alan) - Maineville, Ohio; brother: William Cunningham (Carolyn) - Williamston, SC; grandchildren: Holly Bishop (Christopher), Sarah Barr (Ryan), Tyler Hydrick (Mandy), Taylor Hydrick (now with our Lord), Shelby Cunningham (Farkhat) and Madison Cunningham; great-grandchildren: Trenton, Mckenli, Ava, Beckett, Allen, Remington, Elsie, Arthur, Sutton-Ann, and two more on the way; and a host of extended family and friends.
Funeral Services will be held 11 AM, Friday April 3, 2026 at Calvary Baptist Church, 1532 Long Bay Road, Middleburg, FL with visitation held 1 hour prior to service. Burial will follow with full military honors at Holly Hill Funeral Home and Memorial Park, 3601 Old Jennings Road, Middleburg, FL.
Please post words of comfort at www.hollyhillfunerals.com.
The Service will be live streamed on Calvary Baptist Church's website.
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