Cottafava joined U.S. Triestina Calcio in 2008. He played for the club in Serie B for 2 seasons. In 2010, he was suspended by the club for 6 months. The club did not award any squad number to him and excluded him from squad and put him to transfer list, but failed to sell him due to his high accounting value of €420,000. He was awarded no.90 shirt and played the first game of the season on 9 January 2011. He left the club after the club relegated.
In June 2009, he was sold to Chievo in co-ownership deal along with Dario D'Ambrosio, which Cottafava's half right was valued for €420,000 and D'Ambrosio €340,000. In return, Amedeo Calliari and Nicolò Brighenti also signed by Triestina in co-ownership deal, for €325,000 and €425,000 respectively. Thus, the swap deal only involved €10,000 from Chievo to Triestina. D'Ambrosio and Cottafava then returned to Triestina on loan and Brighenti and Calliari were loaned to Lega Pro. The deal made Triestina received a player profit of €840,000 and €620,000 respectively, despite it was false, as the club received nothing but two youth players with speculative potential. On 30 June 2009 the club had a net equity of €2,933,043, which if excluding aforementioned €1.46 million player profit, the club had even worse accounting result of €1,473,043. In January 2010 Triestina bought back D'Ambrosio in 4-year contract and sold Brighenti for €425,000 each. After Triestina re-admitted to Serie B in August 2010, Cottafava was bought back by Triestina for €210,000. and Calliari returned to Chievo for €220,000, thus a reverse flow of cash of €10,000. Both D'Ambrosio, Cottafava became the financial burden of Triestina as their accounting value €850,000 and €420,000 had to be amortize as a repayment of false profit gained in June 2009. On Chievo side, Brighenti's €850,000 and Calliari's €440,000 also became a burden for the club, which both were sold in a lower price and Chievo had to write-off the rest as a cost.
In September 2011 he joined Gubbio, the newcomer of Serie B. Gubbio also relegated in 2012. In August 2012 he joined U.S. Latina Calcio of third division. He won promotion to Serie B with the club. After "out of contract" for 10 days, on 11 July 2013 Latina offered him a new contract for 2013–14 Serie B.
