After crossing the river into Mississippi and winning the Battle of Port Gibson, Grant began moving east, intending to turn back west and attack Vicksburg.

Neither commander was aware of the strength of his opponent, and Gregg acted aggressively, thinking McPherson's force was small enough that his men could easily defeat it.

Early in the Civil War, Union military leadership developed the Anaconda Plan, which was a strategy to defeat the Confederate States of America (a significant component of which was controlling the Mississippi River.

[2] The strategically important city of Vicksburg, Mississippi was still in Confederate hands, serving both as a strong defensive position by commanding the river and as the linchpin between the two halves of the Confederacy.

[5][6] In late November, about 40,000 Union infantry commanded by Major General Ulysses S. Grant began moving south towards Vicksburg from a starting point in Tennessee.

Meanwhile, another arm of the expedition under the command of Major General William T. Sherman left Memphis, Tennessee on the same day as the Holly Springs Raid and traveled down the Mississippi River.

After diverting up the Yazoo River, Sherman's men began skirmishing with Confederate soldiers defending a line of hills above the Chickasaw Bayou.

Attacking the enemy from across the river, Grant could have risked heavy casualties, but pulling his men back to Memphis could have been interpreted as a retreat and politically disastrous.

On April 29, Union Navy ships bombarded Confederate river batteries at Grand Gulf in preparation for a crossing, but they did not silence the position.

[10] Grant drove inland with 24,000 men, defeating an 8,000-man Confederate blocking force at Port Gibson on May 1; the batteries at Grand Gulf were abandoned the next day.

Grant put his plan in motion by having Sherman's XV Corps cross the Mississippi River at the now-abandoned Grand Gulf position and then drive towards Auburn.

[20] In his only aggressive action at the time,[17] Pemberton sent Gregg a telegram ordering him to take his brigade to Raymond with hopes of intercepting a Union unit rumored to be at Utica.

[22][23] Expecting the main Union assault to come at the Big Black River, Pemberton believed that any movements towards Jackson via Raymond were simply feints.

Gregg sent the cavalry unit down the road towards Utica while keeping the five men for courier service,[22][26] and sent a message to Adams telling him to bring his force to Raymond.

[32] Colonel Calvin H. Walker and the 3rd Tennessee Infantry Regiment were sent to the reverse slope of some high ground northeast of the bridge over Fourteenmile Creek.

Gregg planned to contest his line with Walker's and Granbury's men and then have the Tennesseeans down the Gallatin Road conduct a flanking attack against the Union right.

[33] Heavy undergrowth along the position restricted Gregg's ability to clearly observe the Union forces when they came, preventing an accurate assessment of McPherson's strength.

As the battle grew in intensity, Stevenson began moving his men to a position behind the 8th Michigan Battery but was initially held back until Confederate intentions became clearer.

[63] The battle was growing chaotic due to thick undergrowth and clouds of smoke, and units on both sides fought more and more individuals with less direction from high-ranking officers.

[23][37] At 13:30, a brigade from Union Brigadier General Marcellus M. Crocker's division, commanded by Colonel John B. Sanborn, arrived on the field and moved to support Logan's left flank.

[26][69] Knowing a retreat would break the Confederate line and that his men would suffer casualties if they remained steady, the unit's commander, Colonel Randal William MacGavock, ordered an attack against the 7th Missouri Infantry Regiment,[70] which had recently crossed the creek.

[77] Fighting ended around 16:00,[78] and Union soldiers entered Raymond where they found and consumed a meal of fried chicken and lemonade that area women had prepared for Gregg's men, expecting a Confederate victory.

[86] Thinking that McPherson's corps was insufficient to take Jackson on its own, Grant decided to bring his whole army to bear against the city, abandoning a previous plan to turn west and cross the Big Black River at Edwards and Bolton.

[37] The previously planned movement was viewed as too risky with Johnston and the Jackson garrison left in the Union army's rear,[87] especially as McClernand's men had also encountered part of Pemberton's force elsewhere simultaneously as the battle at Raymond.

[88] McClernand was ordered to move to Raymond, McPherson was to head northeast to Clinton and then strike Jackson, and Sherman was to approach the place from the southwest.

As a result, the Confederates would need to defeat Grant in open battle outside of the defenses of Vicksburg, and Pemberton's army moved east for this purpose.

[93] Bearss describes McPherson's handling of the battle as "not a success" and as "far too cautious or, perhaps worse, timid", citing his piecemeal deployment of his troops and ineffective use of his artillery advantage.

[82] Smith writes that "McPherson did not earn high marks for the handling of his corps" and criticizes him for allowing the Confederates to have the tactical initiative for most of the fighting and for failing to properly coordinate his troops.

[78] Alternatively, writer Kevin Dougherty attributes the Confederate defeat to Gregg's failure to gain an accurate assessment of McPherson's strength and the nature of the battlefield situation.

[104] As of 2010, about 79 percent of the battlefield at Raymond was still considered intact,[102] including the Union artillery position, Fourteenmile Creek, and part of the Utica Road.