They arrived at Boulogne at 6.30pm, just after a heavy German air raid that General Nehring claimed disabled three destroyers. The new ships were met by HMS Whitshed outside the harbour. Her commander, E. R. Conder, was now the senior naval officer present. He sent a message to Admiral Ramsey, the overall commander of the evacuations, reporting that he would not risk entering the port without air support. Fifty minutes later, at 7.20pm, with RAF fighters overhead the British flotilla began to enter the port.

HMS Whitshed and HMS Vimy went in first. They were each able to take on around 1,000 men, before withdrawing at 8.20pm. They were then followed in by HMS Wild Swan, HMS Venomous and HMS Venetia. HMS Venetia soon became the only British destroyer to be seriously damaged. Her captain was wounded and she was forced to back out of the port. All three ships became involved in a close range ship-to-shore battle, attacking German tanks with their quick firing naval guns, aiming over open sights at enemies only a few hundred yards away. The situation was made worse when the Germans captured the French coastal gun batteries largely intact, and turned them on the British ships. Despite this, at 9.30 HMS Wild Swan and HMS Venomous left port with 900 men on board between them.

By this point 2,900 men had been evacuated, but there were still 2,200 British soldiers in Boulogne. At 10.30pm an eighth destroyer, HMS Windsor reached the port, and was able to evacuate 600 men, amongst them many of the wounded and a naval demolition party that had first been sent in on 22 May. Finally, in the early hours of 24 May HMS Vimiera made the final trip into Boulogne. By now the fighting had died down for the night, and by 2.45 she had been able to take 1,300 men on board. A total of 4,360 men were rescued. Unfortunately a second destroyer, HMS Wessex, had failed to arrive, and so 300 men of the Welsh guard had to be left behind.