In December 1855, Tsar Nicholas I wrote to Prince Alexander Menshikov, the Russian Commander-in-chief for the Crimean War, demanding that the reinforcements being sent to Crimea be put to a useful purpose and expressing a fear that enemy landings at Eupatoria were a danger. The Tsar feared rightfully so that additional Allied forces at Eupatoria, located 75 kilometers north of Sebastopol, could sever Crimea from Russia at the Isthmus of Perekop cutting-off the flow of communications, materials, and reinforcements.

Shortly thereafter, Prince Menshikov informed his officers on Crimea that Tsar Nicholas insisted that Eupatoria be captured and destroyed if it could not be held. To conduct the attack, Menshikov added that he had been authorized to use the reinforcements currently en route to Crimea including the 8th Infantry Division. Menshikov then acted to select a commanding officer for the attack to which his first and second choices both declined the assignment, making excuses to avoid leading an offensive that neither believed would have a successful outcome. Ultimately, Menshikov selected Lieutenant General Stepan Khrulev, an artillery staff officer described as willing to "do exactly what you tell him," as the officer in overall charge of the undertaking.

At approximately 6 am, the first shots were fired when the Turks began a general cannonade supported by rifle fire. As quickly as they could respond, the Russians began their own artillery fire. For about an hour both sides continued to bombard each other. During this time, Khrulev reinforced his column on the left, advanced his artillery to within 500 meters of the city walls, and began to concentrate his cannon fire on the Turkish center. Although the Turkish guns were of a larger caliber, the Russian artillery began to have some success in the cannonade. Shortly thereafter when the Turkish fire slackened, the Russians began to advance five battalions of infantry toward the city walls on the left.

At this point, the attack effectively stopped. The ditches were filled with water at such a depth that the attackers quickly found themselves unable to scale the walls. After numerous failed attempts to cross the ditches and ascend their ladders to the top of the walls, the Russians were forced to retreat and seek shelter back at grounds of the cemetery. Seeing their enemy's difficulties, the Turks took advantage of the situation and sent a battalion of infantry and two squadrons of cavalry out of the city to pursue the Russians as they fell back.

Almost immediately, Khrulev deemed the ditches as an obstacle that could not be overcome and came to the conclusion that Eupatoria could not be taken given its defenses and complement of defenders. When asked with regard to the next steps, Khrulev ordered his forces to retreat. The order was communicated to the commanders of the right and center columns, neither of which had engaged in the fight to the degree as the effort of the left column.