The Confederate defenses were manned by the Fourth Corps of the Army of Northern Virginia under the command of Lieutenant General Richard H. Anderson.

Reinforced by a four-gun artillery battery and later relieved by two large regiments from the brigade commanded by Colonel (Brevet Brigadier General) Edgar M. Gregory, the Union troops ultimately forced the Confederates back to their defenses and captured an important road junction.

Union Colonel (Brevet Brigadier General) Alfred L. Pearson was awarded the Medal of Honor 32 years later for his heroic actions at the battle.

On June 15–18, 1864, two Union Army corps, moved unobserved from the stalemated battle lines just north of Richmond across the James River to the south of Petersburg, Virginia.

[9] With supplies and men increasingly hard for Lee to obtain or replace, he knew that his army could not defend Petersburg and Richmond from the growing Union forces indefinitely, especially with the expected arrival of Union reinforcements from recent recruits in training, Major General Philip Sheridan's cavalry divisions from the Shenandoah Valley and possibly even Major General William T. Sherman's armies already operating in North Carolina when the roads dried out after spring rains abated.

[10][11][12] After the Battle of Hatcher's Run on February 5–7, 1865 extended the lines another 4 miles (6.4 km), Lee had few reserves after manning the new defenses.

[11][19][20] Lee accepted Major General John B. Gordon's proposal to attempt to break the Union lines and threaten their supply base at City Point, Virginia by attacking along a narrow front near Fort Stedman, east of Petersburg and south of the Appomattox River, in order to compel Grant to shorten his lines, at least temporarily.

[21] If successful, this could give Lee an opportunity to shorten his lines and an opening and head start in a movement to the west and toward North Carolina.

He also knew that Grant would soon move against the only remaining Confederate supply lines to Petersburg, the Southside Railroad and the Boydton Plank Road, beyond the end of his current defenses.

[27] Otherwise, Sheridan should wreck the railroads as much as possible and either return to the Petersburg lines or join Sherman in North Carolina at his discretion.

Grant wanted these infantry corps to outflank the Confederates in their defenses and prevent them from interfering with Sheridan's mission, pushing them back to their lines if they came out to fight.

[27] Warren's corps initially also was ordered to seize Dinwiddie Court House, Virginia, which also would capture a portion of the Boydton Plank Road at that location, but later that task was given to Sheridan.

[29] A good verbal description of the roads and positions in the area, given by Brigadier General Joshua Chamberlain in his 1915 book The Passing of the Armies, is recited in the footnote.

[30][31][32] Warren reported to his immediate superior, Major General George G. Meade, who remained in direct tactical command of the Army of the Potomac, that Dinwiddie Court House was undefended.

[38] After leading the brigade about 1.5 miles (2.4 km) north on Quaker Road, Chamberlain's skirmishers reported that the bridge over Gravelly Run had been destroyed and that Confederates were entrenched on the other side.

Chamberlain and the regiment's officers steadied the men and soon they pushed the Confederates back until Union artillery under Regular Army Lieutenant John Mitchell came up with four guns to support them.

Colonel (Brevet Brigadier General) Alfred L. Pearson led the Pennsylvanians to the center and toward the sawdust pile that the Confederates were using for cover.

Pearson grabbed the regimental colors and charged toward the sawdust pile with his men following and passing through the ranks of the exhausted First Brigade.

[61] Having to deal with muddy roads over a longer route, Sheridan's cavalry divisions reached Dinwiddie Court House at about 5:00 p.m. on March 29, 1865.

[15] Lee had only 6,000 cavalry north of the James River or at Stony Creek Depot, 18 miles (29 km) south of Petersburg and about 5,000 effective infantry that he could send to extend his line to the west to counter the anticipated Union movement.

[15] In the morning on March 29, Lee prepared to have Major General George Pickett take this force to Sutherland Station and move to protect Five Forks in Dinwiddie County.

[15] Lee ordered Pickett to take the brigades of Brigadier Generals William R. Terry, Montgomery Corse and George H. Steuart on the Southside Railroad to Sutherland Station, 10 miles (16 km) west of Petersburg, and he ordered Brigadier General Eppa Hunton to be ready to move to reinforce Pickett or to defend the junction of the Southside and Richmond and Danville Railroads at Burkeville, Virginia.

Besides moving Brigadier General Samuel McGowan's brigade farther west to extend Johnson's line along White Oak Road, he thinned the White Oak Road line further by moving Brigadier General William MacRae's brigade to the west.

Nonetheless, a gap continued to exist between Pickett's force and McGowan's brigade at the end of the Confederate White Oak Road Line.

[75] The lead brigade under Colonel Frederick Winthrop crossed a swollen branch of Gravelly Run which was to feature in the following day's battle.