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May 5, 1862 Battle of Williamsburg

Major General James Longstreet [CS] nearly defeats Major General "Fighting Joe" Hooker [US] during a rear-guard action.
Virginia
  Peninsula Campaign
  James Longstreet
  Lafayette McLaws
  George McClellan
  Battle of Williamsburg
  William Farrar Smith
  Winfield Scott Hancock
  Jubal Anderson Early
  Joseph Hooker
  Samuel Garland
  Samuel Heintzelman
May 5, 1863 Former representative and a leader of the Peace Democrats, Clemont Vallandigham is arrested by the federal army. Ohio
  Clement Vallandigham
May 5, 1864
May 7, 1864
Battle of the Wilderness

Ulysses S. Grant [US] is badly beaten on the field by Robert E. Lee [CS] but rather than retreat, Grant advances to Spotsylvania Court House.

Union: 17,666

Confederate: 7,750
Virginia
  Bloodiest Civil War battles
  Robert E. Lee
  Ulysses S. Grant
  Army of Northern Virginia
  Overland Campaign
  James Longstreet
  Winfield Scott Hancock
  A. P. Hill
  Richard Ewell
  Gouverneur K. Warren
  John Sedgwick
May 5, 1864 Army of the James under General Benjamin Butler [US] lands at Bermuda Hundred and City Point, east of Petersburg. The Army is comprised of two corps totaling nearly 40,000 men. Virginia
  Benjamin Butler
  Quincy A. Gillmore
  William Farrar Smith
May 5, 1864 William W. Averill [US] leaves Logan Court House with orders to destroy the the Virginia and Tennessee Railroad West Virginia

Ongoing on this day:
April 12, 1861
May 10, 1865
The American Civil War
  The Civil War
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