Salerno, in Southern Italy, opened the first University in Europe including a Medical Faculty in the eleventh century CE. Remarkably, their courses were open to both genders! The city was a Mediterranean port, South of Naples, which fused influences of Arab and Byzantine-Greek culture. It became a stopover city on the Crusade route. The school had benefited from the teachings of Constantine the African in 1077 and his translation of many texts back from Arabic to Latin. The Medical School of Salerno was initially sanctioned by the church and grew in reputation and size becoming a point of attraction for both the sick and students of medicine from all over Europe. This chapter then reviews the struggle and achievements of women from the late Middle Ages to the Twenty-first century, as they “Dared to Dream of Equality” and to be fully accepted into the professions of first, medicine, and then surgery, and the overcoming the barriers of limited opportunity, lack of acceptance by a then male dominated profession, and the right to progress their careers whether in the military or academia. The achievements of the pioneers such as Harriet Hunt and Elizabeth Blackwell in America, Elizabeth Garrett Anderson and Sophia Jex Blake in England in the 19th century blazed trail that led to there being 7000 women doctors in the USA in the year 1900, whilst there were only 258 in the UK and 95 in France, where Madeline Brès was the first female to qualify. The chapter reviews the pioneer women from Russia, Denmark, Sweden, China, India and Latin America before addressing the challenges faced in the 20th century and those that became leaders of their Departments and Profession. The chapter finishes with a brief review of bullying, discrimination and sexual harassment in surgery including the #MeToo movement and the ongoing struggle for equal pay and the efforts of Surgical Colleges to promote gender equity.