[1] Together with his elder brother and eventual three-time Olympian Gianfranco, he was named one of the country's top sailors in the skiff boat for two Summer Olympic editions (2004 and 2008) and came close to the medal haul in Beijing (finishing in fourth place).

A fusion of scores varying from a couple of fourths to a lowly seventeenth under shifty conditions, however, pushed the Italians to the middle of the fleet and never looked back, sitting them in fourteenth overall with a net grade of 138.

2 crew, the Sibello brothers enjoyed the race series comfortably with two straight victories in the third and fourth leg and a random wave of top-five marks along the way to cement their place for the medal round.

[10][11] Lying in the runner-up position, they battled against the Aussies to the front under gusty conditions, until their boat capsized at the final upwind mark let the Spanish, German, and British crews overtake them.

[2][12][13] Sibello sought to bid for his third consecutive trip to the Games in London 2012 with Gianfranco after receiving a quota place at the 49er Worlds in Zadar, Croatia; however, the committee's sports medical commission ruled him ineligible to compete for the Italian sailing team, citing health problems.