Yes, according to the official lore surrounding the movie One Piece: Stampede, Douglas Bullet and Sir Crocodile fought in the past, and the battle remarkably ended in a draw. This event took place when both characters were in their late teens or early twenties (around ages 19 and 20). At the time, Bullet was already a powerhouse who had been a member of the Roger Pirates, while Crocodile was a rising rookie. The fact that Crocodile managed a stalemate against a man often compared to Silvers Rayleigh in strength is a testament to his early prowess, before his crushing defeat by Whitebeard led him to a more cynical path in Alabasta. While this rivalry is mostly detailed in promotional materials and the Vivre Card databooks rather than the main manga series, it is considered a significant part of the characters' shared history, illustrating that even the most legendary antagonists had fierce rivals during their climb to power.