First Battle of Deep Bottom The First Battle of Deep Bottom , also known as Darbytown , Strawberry Plains , New Market Road , or Gravel Hill , was fought July 27 – 29 , 1864 , at Deep Bottom in Henrico County , Virginia , as part of the Siege of Petersburg of the American Civil War . A Union force under Maj . Gens . Winfield S . Hancock and Philip H . Sheridan was sent on an expedition threatening Richmond , Virginia , and its railroads , intending to attract Confederate troops away from the Petersburg defensive line , in anticipation of the upcoming Battle of the Crater . The Union infantry and cavalry force was unable to break through the Confederate fortifications at Bailey ' s Creek and Fussell ' s Mill and was withdrawn , but it achieved its desired effect of momentarily reducing Confederate strength at Petersburg . Background . Deep Bottom is the colloquial name for an area of the James River in Henrico County southeast of Richmond , Virginia , at a horseshoe - shaped bend in the river known as Jones Neck . It was a convenient crossing point from the Bermuda Hundred area on the south side of the river . Lt . Gen . Ulysses S . Grant began a siege of the city of Petersburg , Virginia , after initial assaults on the Confederate lines , June 15 – 18 , 1864 , failed to break through . While Union cavalry conducted the Wilson - Kautz Raid ( June 22 – July 1 ) in an attempt to cut the railroad lines leading into Petersburg , Grant and his generals planned a renewed assault on the Petersburg fortifications , an attack scheduled for July 30 that would become known as the Battle of the Crater . Hoping to increase the chances for success at Petersburg , Grant planned a movement against Richmond that Gen . Robert E . Lee would likely counter with troops taken out of the Petersburg line . Grant ordered the II Corps of the Army of the Potomac , commanded by Maj . Gen . Winfield S . Hancock , and two divisions of Maj . Gen . Philip H . Sheridan ' s Cavalry Corps to cross the river to Deep Bottom by pontoon bridge and advance against the Confederate capital . A division of the X Corps ( Army of the James ) , commanded by Brig . Gen . Robert S . Foster , had previously crossed on a second pontoon bridge just upstream to secure a bridgehead on the north bank of the river . Grant ' s plan called for Hancock to pin down the Confederates at Chaffin ' s Bluff and prevent reinforcements from opposing Sheridan ' s cavalry , which would attack Richmond if practicable . If not — a circumstance Grant considered more likely — Sheridan was ordered to ride around the city to the north and west and cut the Virginia Central Railroad , which was supplying Richmond from the Shenandoah Valley . The Confederate fieldworks protecting Richmond were commanded by Lt . Gen . Richard S . Ewell . When Lee found out about Hancock ' s pending movement , he ordered that the Richmond lines be reinforced to 16 , 500 men . The four brigades of Maj . Gen . Joseph B . Kershaw ' s division joined Col . John S . Fulton ' s brigade of the Department of Richmond and the brigades of Brig . Gens . James H . Lane and Samuel McGowan from Maj . Gen . Cadmus M . Wilcox ' s division . The reinforcements moved east on New Market Road ( present - day Virginia State Route 5 ) and took up positions on the eastern face of New Market Heights . Battle . July 27 . Hancock and Sheridan crossed the pontoon bridge starting at 3 a . m . , July 27 . The II Corps advanced with the division of Maj . Gen . John Gibbon on the left , Brig . Gen . Francis C . Barlow in the center , and Brig . Gen . Gershom Mott on the right . They broke through the Confederate rifle pits on the New Market Road , captured four cannons , and continued to advance towards the Long Bridge Road . After being distracted by Confederate artillery fire , which Mott ' s infantry was able to suppress , the II Corps took up positions on the east bank of Bailey ' s Creek , from New Market Road to near Fussell ' s Mill . Sheridan ' s cavalry rode to the high ground on the right , overlooking the millpond . The cavalry division of Brig . Gen . Alfred T . A . Torbert captured the high ground near Fussell ' s Mill , but they were counterattacked and driven back by the 10th and 50th Georgia Infantry regiments . The Confederate works on the west bank of Bailey ' s Creek were formidable and Hancock chose not to attack them , spending the rest of the day performing reconnaissance . While Hancock was stymied at Bailey ' s Creek , Robert E . Lee began bringing up more reinforcements from Petersburg , reacting as Grant had hoped . He assigned Lt . Gen . Richard H . Anderson to take command of the Deep Bottom sector and sent in Maj . Gen . Henry Heth ' s infantry division and Maj . Gen . W . H . F . " Rooney " Lee ' s cavalry division . Troops were also hurriedly detailed from the Department of Richmond to help the man the trenches . July 28 . On the morning of July 28 , Grant reinforced Hancock with a brigade of the XIX Corps , which freed up Gibbon ' s division from its position on the New Market Road to assist in an attack on the Confederate left . Sheridan ' s men attempted to turn the Confederate left with an advance against Gravel Hill , but their movement was disrupted by a Confederate attack . Three brigades — Lane ' s , McGowan ' s , and Kershaw ' s ( his original brigade before he became division commander ) — attacked Sheridan ' s right flank . The Union cavalrymen formed a battle line in which they were lying prone just beyond a shallow ridgeline . The Confederates charged over the crest and encountered heavy fire from the Union repeating carbines . Mounted Federals in Sheridan ' s reserve pursued and captured nearly 200 prisoners ; the Confederates were able to capture a single Union cannon before withdrawing to their earthworks . Aftermath . By the afternoon of July 28 , Hancock had repositioned his divisions to ensure that his force could return to the Deep Bottom crossing point without interference . No further combat occurred and the expedition against Richmond and its railroads was terminated . Satisfied that the operation had distracted sufficient Confederate forces from his front , General Grant determined to proceed with the assault against the Crater on July 30 . He ordered Hancock to send Mott ' s division to the Petersburg trenches that night so that the XVIII Corps could take up a position to support the assault . The remainder of the II Corps and the cavalry recrossed the James on July 29 . Union casualties at the First Battle of Deep Bottom were 488 ( 62 killed , 340 wounded , and 86 missing or captured ) ; Confederate casualties were 679 ( 80 killed , 391 wounded , 208 missing or captured ) . The Second Battle of Deep Bottom would be conducted in essentially the same area , August 13 – 20 , 1864 .