Sheridan's men gave way at various locations during the day but fought long and hard delaying actions, keeping their organization after withdrawals and inflicting hundreds of casualties on the Confederates.

During the 292-day Richmond–Petersburg Campaign (Siege of Petersburg) Union General-in-Chief Ulysses S. Grant had to conduct a campaign of trench warfare and attrition in which the Union forces tried to wear down the less numerous Confederate Army of Northern Virginia, destroy or cut off sources of supply and supply lines to Petersburg and Richmond and extend the defensive lines which the outnumbered and declining Confederate force had to defend to the breaking point.

[7][8][9] After the Battle of Hatcher's Run on February 5–7, 1865 extended the armies' lines another 4 miles (6.4 km), Lee had few reserves after manning the lengthened Confederate defenses.

Lee, who was already concerned about the ability of his weakening army to maintain the defense of Petersburg and Richmond, realized that the defeat at Fort Stedman would encourage Grant to make a move against his supply lines and right flank.

[35] The trains shuttling the troops to Sutherland Station were so slow that it was late night before the last of Pickett's men reached their destination, 10 miles (16 km) west of Petersburg.

Lee wanted to control this intersection in order to keep open the South Side Railroad and important roads and to drive the Union force back from its advanced position at Dinwiddie Court House.

[56] Earlier on March 30, a day of steady torrential rain, General Lee met with several officers including Anderson, Pickett and Heth at Sutherland Station.

[2] With the 4 miles (6.4 km) gap between the end of the Confederate White Oak Road Line southwest of Petersburg and Pickett's force at Five Forks in mind, on March 30, Lee made additional deployments to strengthen his right flank.

After discussing the situation, Pickett decided because of the late hour and the absence of the other cavalry divisions to wait until morning to move his tired men against Sheridan at Dinwiddie Court House.

[60] As the rain continued on March 30, Grant sent a note to Sheridan in which he said that cavalry operations seemed to be impossible and perhaps he should leave enough men to hold his position and return to Humphreys' Station for forage.

[64] During their discussions, Grant told Sheridan he would send him the V Corps for infantry support and that his new orders were not to extend the line further but to turn the Confederate flank and to break Lee's army.

Wise and Colonel Martin L. Stansel in lieu of the ill Young Marshall Moody,[68][70][71] reinforced by the brigades of Brigadier Generals Samuel McGowan and Eppa Hunton, attack the exposed Union line.

[84] Soon after Davies's patrol reached their station, his men spotted both Confederate cavalry and infantry heading toward Dinwiddie Court House on the west side of the creek.

[91] Pickett had decided to march south from Five Forks on Scott Road at about 9:00 a.m. for an attack on Sheridan at Dinwiddie Court House despite the bad weather and the hunger of his ill-fed troops.

[93] Colonel (Brevet Brigadier General) J. Irvin Gregg's brigade stood in reserve at the junction of Adams and Brooks roads, midway between the two crossings.

[98] Pickett decided to go back north for 1 mile (1.6 km) to cross at Danse's Ford with his three infantry brigades (Corse's, Terry's and Steuart's) and Rosser's cavalry.

Davies rode ahead and discovered that Smith had stabilized the situation, throwing those troopers of Barringer's brigade who had managed to cross the creek back across it.

[109] At Sheridan's instruction, Merritt then ordered Devin to take Fitzhugh's and Stagg's brigades to the Boydton Plank Road and move to Dinwiddie Court House.

[111] He deployed the 6th Michigan Volunteer Cavalry Regiment to drive back Munford's suddenly pursuing Confederates, which they accomplished with their Spencer repeating carbines.

[110][111] Davies then sent Fitzhugh and Stagg to Dinwiddie Court House on a wide movement to and over the Boydton Plank Road where they were rejoined by their men with their led horses.

[114] Upon Sheridan's order to support and relieve the brigades of Crook's division Custer deployed about three-quarters mile north of Dinwiddie Court House.

[119][120] On the left, Fitzhugh Lee's cavalry attacked Smith's men, who continued to hold out despite heavy losses, until they finally ran out of ammunition near dark.

[113] "By presenting a good front, without a cartridge," Smith's retiring force discouraged a further attack against them as they occupied a stronger position further south and pretended they had ammunition.

Sheridan's delaying actions were effective at several points but the Union cavalry was pushed back almost to Dinwiddie Court House by the end of the day.

[131] Sheridan appears not to have been as confident as he led Porter to believe because in a letter to Grant sent with a later dispatch via an aide, Colonel John Kellogg, he wrote that "This force (Pickett's) is too strong for us.

[137] At about 6:30 p.m., when Meade learned more about the location of Pickett's and Sheridan's forces, he ordered Warren to send his relief column down the Boydton Plank Road, but Bartlett had been gone too long to be easily recalled.

[138] Warren sent three regiments that Bartlett had detached to guard artillery and wagons down the Boydton Plank Road under Colonel (Brevet Brigadier General) Alfred L. Pearson and reported this to Meade.

[144] When Grant then notified Sheridan that the V Corps and Ranald Mackenzie's cavalry division from the Army of the James had been ordered to his support, he gratuitously and without any basis said that Warren should reach him "by 12 tonight.

[164] Pickett realized his position was untenable after he learned between 9:00 p.m. and 10:00 p.m. that Bartlett's brigade was on its way to reinforce Sheridan, exposing his force to flanking Union infantry attack.

[153][154][165] Bartlett's brigade was only the lead unit for all of Griffin's and Crawford's divisions which were put on the march later that night and would have trapped Pickett's force between them and Sheridan's troops.