Guccione gained his first playoff experience in 2010, umpiring the 2010 American League Division Series between the New York Yankees and the Minnesota Twins. He has worked a total of seven Division Series (2010, 2011, 2013, 2014, 2015, 2016, 2020), four League Championship Series (2012, 2017, 2018, 2019) and two World Series (2016, 2020). According to an analysis done by the website FiveThirtyEight, he was the most accurate umpire in the major leagues in 2014 Major League Baseball season based on the number of unsuccessful manager challenges; 14 of his 15 calls that were challenged were upheld on video review.