The first shots in Endo's battle to seize Topside were fired by F Company 1000 yards east of Wheeler Point at 10:30 PM the night of the 18th when a 500 man force of shouting, cheering Japanese in the eastern attack force came out of the Battery Smith magazine charging four abreast down Belt Line Road toward Battery Hearn.  In a fierce protracted night battle, F Company's riflemen at Battery Hearn stopped the marines dead in their tracks. Private Lloyd McCarter would win the Medal of Honor that night for his part in the battle. The first phase of Endo's plan for his eastern column to storm Topside Barracks by attacking down Beltline Road ended in dismal failure.  The marines suffered heavy casualties at the hands of F Company riflemen and only a mere handful of the marines would ever reach the parade ground and they would be dispatched quickly by the headquarters troops quartered there.  The second part of the attack would begin a few hours later after Endo's western column had marched noiselessly up Cheney Ravine to battle the intrepid rifleman of D Company in the early morning darkness.

It was sometime after one o'clock in the morning when nearly 900 Japanese marines under Lieutenant Endo assembled near the western end of Cheney Trail. The column quickly and quietly climbed up the winding trail, cut out of the steep western wall of Cheney Ravine and finally reached Topside 500 feet above the rocky western beaches, they had left more than an hour ago.  Lieutenant Endo must have been greatly pleased by his good fortune when he reached the high ground at Topside without being discovered. His attack column walked to within 50 yards of the two 2d platoon squads, looking down from their perches high above Cheney Trail in the rear of Battery Cheney, but the men neither heard nor saw the Japanese attackers in the black moonless night.