On January 25, 1944, Montgomery impressively knocked out powerful Black lightweight Ike Williams in the twelfth round at Convention Hall in Philadelphia. Montgomery hammered Williams repeatedly in the first eleven rounds. As Williams walked out of his corner for the twelfth round, Mongtomery tagged him with a series of straight rights that twice floored him for eight counts. Upon rising, Montgomery floored Williams for the final count with a right to the jaw, and he went down by the ropes. Williams would take the World Lightweight Championship in April 1945, holding it for several years.