Complex sentence: Caulfield started his career in women's football when he was offered the Manager's job of Monklands Ladies in the summer of 1997 and guided them in his first season in charge to the 1997/98 Scottish Women's 1st Division West title.
Split into simpler sentences: Caulfield started his career in women's football when he was offered the manager's job of Monklands Ladies in the summer of 1997. In his first season in charge he guided them to the 1997--98 Scottish Women's 1st Division West title.