In June 1941, the Lebanese coastal town of Sidon had a population of approximately 12,000 people. It was the largest town that the 21st Australian Brigade, advancing along the coast after crossing the Palestine frontier on 8 June, had thus far encountered. Due to the presence of the large civilian population and a great deal of historic architecture, the Australians at first sought to parley with Sidon's Vichy French defenders. They were rebuffed by artillery fire and the 2/16th Battalion were ordered to attack on 13 June. The plan involved an advance of six and a half kilometres, across open country in daylight, to Sidon, and then a further advance of four and a half kilometres beyond it. A and D Companies would advance side by side, on the left and right respectively, and C and B would follow a little under a kilometre to the rear. The infantry were to be supported by artillery fire from the 2/4th Field Regiment.
Crossing the start line at 10am, A Company, despite encountering machine gun posts and tanks, made steady progress and reached its objective about 3pm. Once there, however, there was no sign of either D Company to the left, or C Company behind. Isolated and vulnerable, it withdrew until it encountered C Company, which had been held up by prowling Vichy French tanks, south of Sidon. In the meantime, D and B Companies had been fighting for their very existence. As they passed Sidon's eastern outskirts they were heavily attacked by eight Vichy French tanks supported by mortars and infantry. Both company commanders were killed and, with no effective weapons with which to tackle the tanks, the companies scattered. Two anti-tank guns were brought forward but, firing at extreme range, made little impact, and it was only the direct fire of two 25 pounders that was able to curb the exuberance of the tanks and allow the infantry to escape. During the battle the 2/16th's headquarters, and the exposed positions of the 2/4th Field Regiment were also heavily attacked by Vichy French aircraft. The heavy casualties suffered by the 2/16th on 13 June led to becoming known as 'Black Friday' within the battalion.
Throughout 14 June the 2/16th held positions south of Sidon. The Vichy French attempted an attack late in the afternoon but this was broken up by artillery fire. That day the 2/27th Battalion unsuccessfully attacked Vichy positions at Miyeoumiye, in the hills south-east of Sidon. The next morning, however, their patrols found that the Vichy French had withdrawn form the whole Sidon area and by early afternoon troops of both the 2/27th and 2/16th Battalions had entered the town. The 2/16th did not stay long. It left a company in Sidon, and trudged on to the original objectives of Black Friday.