In the latter part of August, 1864, his regiment moved to the right in front of Richmond at Deep Bottom. It was at this point that his regiment made its brilliant and famous charge on the 29th day of September, 1864. And it was there that Sergeant Major Holland led the assaulting company of his regiment in their famous charge. Brilliant as had been its past record, and courageous as the men had shown themselves to be on other fields, this one occasion seems to have been reserved as the crucial test of their fighting qualities. When they met the enemy, they fought hand to hand with a desperate valor that beggared description. The shot and shell of the enemy mowed down the front ranks of the colored troops like blades of grass beneath the sickle’s deadly touch. But, with a courage that knew no bounds, the men stood like granite figures. They routed the enemy and captured the breastworks. The courage displayed by young Holland’s regiment on this occasion called for the highest praise from General Grant who personally rode over the battlefield in company with Generals Butler and Draper.
Holland was wounded in this battle but did not leave the field. Later in the day the regiment made a charge at Fort Harrison to relieve a brigade of white troops that was unable to get back to the Union lines.
Immediately after the charge at New Market Heights, Holland was examined on the field by order of General Butler and passed for captain, but was, on account of color, refused his commission by the War Department. Twice he was presented with medals which were awarded him for bravery and distinguished services on the field of battle. One of these medals was voted him by Congress and forwarded to him through President Lincoln, and the other was awarded by General B. F. Butler [the Congressional Medal of Honor and the Butler Medal.]
He served with his regiment at Dutch Gap until October 4th, when the regiment went over to Fair Oaks, or Seven Pines, where the Union forces achieved a victory of which they were afterwards deprived by a successful ruse of the enemy.
In December, 1864, the regiment went with the great naval fleet under General Butler to Fortress Fisher at the attempt to break up the blockade-running. [When the] regiment landed at Fortress Fisher, they were compelled to withdraw on account of the insufficiency of support. They returned in January, 1865, under command of General Terry when this fort was captured.
He was with his regiment on its marches through Wilmington, Bentonville, Goldsboro, and Raleigh. He was present when General Joseph E. Johnston surrendered to General W. T. Sherman, and it was here that his regiment received the sad tidings of the death of President Lincoln, when men of iron nerves shed tears like broken-hearted children.
After the war, Holland was employed by the Federal Government, working in the Auditor’s Office. He was eventually promoted to chief of collection for the 16th District. In the late 1800’s he founded the Alpha Insurance Company in the District of Columbia, which was one of the earliest insurance companies in the nation owned and operated by an African American. He died from a heart attack on May 15, 1910 and is buried with his wife Virginia in Arlington National Cemetery.