In 2009, Prandelli surpassed Fulvio Bernardini as the longest-serving manager in Fiorentina history, and guided the "viola" to a historic qualification in the round of 16 of the 2009–10 Champions League, where it was eliminated by Bayern Munich (which later went on to reach the final) through the away goals rule. Prandelli, however, did not manage to repeat such successes at the domestic stage, with things being made even more complex by his key player Adrian Mutu being suspended due to doping-related issues. Fiorentina ended the 2009–10 Serie A in 11th position, far removed from the top sides in the league.