14. AC Milan (2005)
AC Milan was the best soccer team on the planet in 2005. Their lineup included all-time-greats like Andrea Pirlo, Kaka, and Paolo Maldini. Analysts favored them to win the Champion’s League when they blazed their way to the final. They faced a resurgent Liverpool in Instanbul and expected to win easily against the Reds.
On paper, Milan was a much better team. They blazed to a 3-0 lead in the first half and it looked like the game was over (via The Guardian). But then Liverpool produced one of the greatest comebacks ever. Milan stumbled and fell flat on their faces before a total collapse. In the end, Liverpool won the game after a penalty shootout. It was high drama and a wasted opportunity for Milan.