Matthew Ray enlisted in Company K of the 4th Mississippi Infantry in Grenada, Mississippi when he was 22 years old June 3 , 1861 his unit being sent to the defense of Fort Donelson, Tenn. He along with 12,000 other confederate soldiers were surrendered to the attacking forces of Ulysses S. Grant on Feb. 16, 1862 in a historic occasion where General Grant responded to the Confederate commander's question for terms of surrender with "I propose no terms other than unconditional surrender".

Seriously ill at the time of his capture, Matthew was sent by authorites to a hospital in St. Louis and after a 5 week stay there he sufficiently recovered to be transferred March 31, 1862 to the Union prison of war facility near Chicago known as Camp Douglas. Camp Douglas during the month of February 1862 had a death rate among its prison population of 10%, the highest single death rate of prisoners for any Civil War prison North or South during the entire war.

Exchanged in August of 1862 he rejoined the 4th Mississippi and was promoted to 2nd Sergeant. He was captured a second time on May 17, 1863 in the battle of the Big Black River which was Confederate General Pemberton's last attempt to prevent Grant's approach and eventual siege of Vicksburg. Matthew's second experience as a prisoner of war resulted in his being interred at Camp Morton, Indiana and Fort Delaware.

Released a second time at City Point, Virginia, under terms of parole that Grant had given the confederates at Vicksburg, surrendered and the prisoners there generously paroled.

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