Just after midnight, Dutch submarine O.16 enters the shallow harbor at Mueang Patani, Thailand, where Japanese are unloading troops and equipment to move into Malaya. O.16 badly damaged 4 Japanese freighters with 6 torpedoes and then escapes, although the ships will be raised and returned to service.
Malaya. At 2 AM, Indian troops blow up the bridge at Jitra and Allied forces begin a headlong retreat 33 miles South to the next defensive line at Gurun. Japanese cross the river at Jitra and, 12 miles South, find the British airfield at Alor Setar abandoned. British have destroyed all the aircraft but Japanese capture bombs and fuel that will be used against the retreating Allies. The commander of 1st battalion /14 Punjab Regiment Major Mohan Singh is taken POW and will, with Japanese encouragement, form First Indian National Army to fight against the British.
Hong Kong. After conducting a fighting retreat, the last Allied troops evacuate Kowloon at 9.30 AM, destroying boats and equipment, and cross to Hong Kong Island.
The 90 mile strait between Cape Bon, Tunisia, and Sicily is the busiest intersection in the Mediterranean. 3 British destroyers HMS Sikh, HMS Maori & HMS Legion and Dutch destroyer HNLMS Isaac Sweers sailing East from Gibraltar to Alexandria encounter 2 Italian cruisers Alberto da Giussano & Alberico da Barbiano plus torpedo boat Cigno sailing South from Palermo carrying fuel and troops to Tripoli for Rommel. At 3:25 AM, British use the well-worn tactic of attacking at night using radar (which the Italian ships lack), sinking both cruisers in 5 minutes (1020 killed, 645 survivors rescued by torpedo boat Cigno or swim to shore).
In the Gulf of Taranto, Italy, British submarine HMS Upright sinks Italian steamers Fabio Filzi & Carlo del Greco, escorted by Italian destroyers Da Recco and Usodimare.
Operation Crusader. Allied troops attack Afrika Korps at Gazala. 5th New Zealand Brigade are held by Germans covering the coast road but 5th Indian Brigade overcomes Italian troops on the inland flank, allowing British tanks to move 15 miles behind the Gazala line where they are halted by 39 German tanks.
British battleship HMS Duke Of York departs the Clyde carrying Winston Churchill to USA, escorted by destroyers HMS Faulknor, HMS Foresight & HMS Matabele.