Cichero began his professional career with Uruguayan Primera División side Montevideo Wanderers, appearing in 35 matches and scoring 1 goal. During January 2006 transfer window he was loaned to Serie A side U.S. Lecce for the remainder of the season. He then returned to Uruguay and in 2007 was transferred to Vihren Sandanski, in the Bulgarian championship. Following his stay in Bulgaria Cichero returned to his native Venezuela and signed with Deportivo Italia.
Cichero was loaned out to Red Bull New York of Major League Soccer on July 11, 2008 in a deal that was to end in December 2008, but had an option to be extended into 2009. Numerous blunders in the handful of key late-season games he played meant that the loan was never extended and Cichero was not offered a contract. After being released by New York, he was loaned out to Caracas FC for the 2009 season.