To protect the approaching convoy from attack by CAF aircraft, Yamamoto sent two battleships from Truk to bombard Henderson Field. At 01:33 on 14 October, and , protected by one light cruiser and nine destroyers, reached Guadalcanal and fired at Henderson Field from a distance of . Over the next one hour and 23 minutes, the two battleships fired 973 shells into the Lunga perimeter, most of them falling in the area of the airfield. Many of the shells were fragmentation shells, designed to destroy land targets. The bombing heavily damaged both runways, burned almost all of the available airplane fuel, destroyed 48 of the CAF's 90 aircraft, and killed 41 men, including six CAF pilots. The battleship force then returned to Truk.
In spite of the heavy damage, Henderson soldiers were able to fix one of the runways within a few hours. Seventeen SBDs and 20 Wildcats at Espiritu Santo were flown to Henderson and U.S. Army and Marine transport aircraft began to transport airplane gasoline to Guadalcanal.
Now that the US was aware of the approach of the large Japanese convoy, the US tried to think of a way to attack the convoy before it could reach Guadalcanal. Using fuel drained from destroyed aircraft and from a hidden fuel tank in the jungle, the CAF attacked the convoy twice on the 14th, but caused no damage.
The Japanese convoy reached Guadalcanal at midnight on 14 October and began unloading. Throughout the day of 15 October, CAF aircraft from Henderson bombed and machine-gunned the unloading convoy, destroying three of the cargo ships. The remainder of the convoy departed that night, having unloaded all of the troops and about two-thirds of the supplies and equipment.
Several Japanese heavy cruisers also bombed Henderson on the nights of 14 and 15 October, destroying a few additional CAF aircraft, but not damaging the airfield.
Between 1 and 17 October, the Japanese delivered 15,000 troops to Guadalcanal, giving Hyakutake 20,000 troops for his planned attack. Because they had lost their positions on the east side of the Matanikau, the Japanese decided that an attack on the U.S. defenses along the coast would be too hard. Hyakutake decided to attack from south of Henderson Field.
His 2nd Division (with troops from the 38th Division), under Lieutenant General Masao Maruyama and 7,000 soldiers in three infantry regiments was ordered to attack the American defences from the south near the east bank of the Lunga River.
The date of the attack was set for 22 October, then changed to 23 October. To try and trick the Americans from knowing about the planned attack from the south, Hyakutake's heavy artillery plus five battalions of infantry (about 2,900 men) under Major General Tadashi Sumiyoshi attacked the American defenses from the west.
The Japanese thought that there were 10,000 American troops on the island, when in there were really 23,000.
On 12 October, a group of Japanese engineers began to cut a trail, called the "Maruyama Road", from the Matanikau towards the southern portion of the U.S. Lunga perimeter. The long trail went across rivers and streams, deep ravines, steep ridges, and thick jungle.
Between 16 and 18 October, the 2nd Division began their march along the Maruyama Road.
By 23 October, Maruyama's forces were finding it hard to get through the jungle to reach the American forces. Hyakutake delayed the attack to 19:00 on 24 October. The Americans did not know that Maruyama's forces were on their way.
Sumiyoshi was told by Hyakutake's staff of the delay of the attack to 24 October. However, he was unable to contact his troops to tell them of the delay. Thus, at dusk on 23 October, two battalions of the 4th Infantry Regiment and the nine tanks of the 1st Independent Tank Company attacked on the U.S. Marine defenses at the mouth of the Matanikau.
U.S. Marine artillery, cannon, and rifle fire defeated the attacks, destroying all the tanks and killing many of the Japanese soldiers. Only a small number of Marines were killed or wounded.
Finally, late on 24 October Maruyama's forces reached the U.S. Lunga perimeter. Over two nights Maruyama's troops attacked positions defended by troops of the 1st Battalion, 7th Marines under Lieutenant Colonel Chesty Puller and the U.S. Army's 3rd Battalion, 164th Infantry Regiment, commanded by Lieutenant Colonel Robert Hall.
U.S. Marine and Army units armed with rifles, machine guns, mortars, and fire from 37 mm anti-tank guns did terrible damage to the Japanese. A few small groups of Japanese that broke through the American defenses, were all killed over the next several days.
More than 1,500 of Maruyama's troops were killed in the attacks while the Americans lost about 60 killed. Over the same two days American aircraft from Henderson Field destroying 14 Japanese aircraft and sunk a light cruiser.
Further Japanese attacks near the Matanikau on 26 October were also defeated with heavy losses for the Japanese. As a result, by 08:00 on 26 October, Hyakutake stopped the attacks and ordered his forces to retreat. About half of Maruyama's survivors were ordered to retreat back to the Matanikau Valley. The 230th Infantry Regiment under Colonel Toshinari Shōji was told to go to Koli Point, east of the Lunga perimeter.
Soldiers from the 2nd Division reached the 17th Army headquarters area at Kokumbona, west of the Matanikau on 4 November. Shoji's unit reached Koli Point and made a camp. The 2nd Division had many battle deaths, combat injuries, malnutrition, and tropical diseases. It was too weak to do any more attacks. It fought as a defensive force along the coast for the rest of the battle.
The Japanese lost 2,200 – 3,000 troops in the battle while the Americans lost around 80 killed.
At the same time that Hyakutake's troops were attacking the Lunga perimeter, Japanese aircraft carriers and other large warships led by Isoroku Yamamoto moved near the southern Solomon Islands. From this location, the Japanese naval forces hoped to defeat any Allied (primarily U.S.) naval forces, especially carrier forces. Allied naval carrier forces in the area, now under the command of William Halsey, Jr., also hoped to meet the Japanese naval forces in battle.
Nimitz had replaced Ghormley with Halsey on 18 October after deciding that Ghormley had become too negative to lead Allied forces in the South Pacific area.
The two opposing carrier forces battled each other on the morning of 26 October, in what became known as the Battle of the Santa Cruz Islands. Each side sent carrier air attacks. Allied ships had to retreat from the battle after one carrier was sunk () and another () heavily damaged. The Japanese carrier forces, however, also pulled back because of high aircraft and aircrew losses and major damage to two carriers.
The Japanese were the winners in terms of ships sunk and damaged. However, the loss by the Japanese of many experienced aircrews helped the Allies, who did not lose many aircrew. The Japanese carriers did not have any more important roles in the battle.
To strengthen his victory in the Battle for Henderson Field, Vandegrift sent six Marine battalions, later joined by one U.S. Army battalion, on an attack west of the Matanikau. The attack was commanded by Merritt Edson and its goal was to capture Kokumbona, headquarters of the 17th Army, west of Point Cruz.
Defending the Point Cruz area were Japanese army troops from the 4th Infantry Regiment commanded by Nomasu Nakaguma. The 4th Infantry was in poor condition because of battle deaths and injuries, tropical disease, and malnutrition.
The American attack began on 1 November. It destroyed Japanese forces defending the Point Cruz area by 3 November. The Americans seemed to be close to capturing Kokumbona. Then American forces found newly landed Japanese troops near Koli Point on the eastern side of the Lunga perimeter.