He was banned by the Italian Tennis Federation in 2015 for betting.
Bracciali won his only ATP singles title in April 2006, at Casablanca, on clay. In the final he beat Nicolás Massú.
In his career, Bracciali has won a total of seven matches at Grand Slam tournaments, six at Wimbledon and one at the Australian Open. In 1998 and 2006, he reached the third round of Wimbledon, his best Grand Slam results. In the first round of Wimbledon in 2005, he defeated Ivo Karlović in five sets after surviving 51 aces from the Croat. He then took Andy Roddick, the previous year's runner-up (and eventual runner-up that year as well), to five sets.
Recently, Bracciali has played primarily doubles. He has won five ATP titles. In 2012, he reached the third round of the 2012 Australian Open partnering Potito Starace. They were beaten by Max Mirnyi and Daniel Nestor. Later that year at the French Open, they reached their first semifinal. They were defeated again by the eventual champions, Max Mirnyi and Daniel Nestor. At Wimbledon, Bracciali partnered the Austrian veteran Julian Knowle and met Mirnyi and Nestor again in the second round. This was the first time that Bracciali won against them. Bracciali and Knowle lost in the quarterfinals to Robert Lindstedt and Horia Tecău.
Bracciali also partnered Roberta Vinci in mixed doubles at the 2012 Australian Open. Entering the draw as an alternate, they reached the semifinals. They lost to the fifth seeds Elena Vesnina and Leander Paes after they took the first set. At the French Open, Bracciali partnered Galina Voskoboeva. They reached the semifinals of the tournament, but lost to the eventual champions Sania Mirza and Mahesh Bhupathi. At Wimbledon, Bracciali teamed up again with Vinci and reached the third round. He played with Vinci at the 2012 Summer Olympics, and with Andreas Seppi in men's doubles at the same event.
In 2013, he reached the quarterfinals of the Australian Open in men's doubles partnering Lukáš Dlouhý. They lost to the Bryan brothers in straight sets.
Following Alessio di Mauro's nine-month ban for betting on matches in November 2007, Bracciali and Potito Starace were each fined and given short suspensions from playing. Bracciali received a fine of £14,300 and a three-month ban from January 1, 2008.
July and November 2007 interceptions between a businessman, Manlio Bruni, and Bracciali were found and they were extensively talking about gaining 50,000 euros each for a set won or lost depending on the match Bracciali was playing. The interceptions were published by several Italian tennis magazines.
In 2015, the Italian Tennis Federation banned Bracciali and Starace lifelong.
Bracciali is known for his powerful serve. His groundstrokes are also reliable, especially his forehand.