Chencinski was born in Bat Yam, Israel, to Jewish parents originally from Poland. He and his family lived in Israel until he was eight years old, before moving to Thornhill, Canada, where he grew up. He attended Chapel School. He speaks both English and Hebrew fluently.
Playing career
College
Chencinski played two years of college soccer at Robert Morris University, where in 2004 he ranked 16th in the nation in saves per game and recorded six shutouts. He transferred to Fairleigh Dickinson University as a junior, where he played his final two collegiate seasons.
He dropped down a division to play in the USL Premier Development League for expansion side Newark Ironbound Express in 2008, but left mid-season when he was offered a contract by Moldova National Division side Nistru Otaci.
After playing just three games for Nistru Otaci, he returned to the United States, and signed for the Harrisburg City Islanders in 2009. After completing his season with the Harrisburg City Islanders, Chencinski spent time training with Major League Soccer side Philadelphia Union.
Expecting to start another season with Harrisburg, Chencinski was given the chance of a week-long trial with Finnish side VPS. After a successful trial, he was signed by the Finnish club to provide competition for the goalkeeper position. He made his debut for VPS on February 5, 2011 in a 2–2 draw with FF Jaro in the Finnish League Cup.
In January 2015, Chencinski left Israel and joined RoPS of Finland. RoPS would eventually finish in 2nd place during the 2015 Veikkausliiga, one point behind league winners SJK. Their finish earned the club entry into the first round of qualification for the 2016–17 UEFA Europa League.
Helsingborgs IF
After his successful season in Finland, Chencinski joined Swedish club Helsingborg on December 8, 2015.
Shamrock Rovers
Chencinski joined Irish club Shamrock Rovers on December 15, 2016. After being the starting goalkeeper for the 2017 season, Chencinski left Rovers midway through his second season with the club after they signed Alan Mannus as a replacement.
International career
Chancinski is eligible to play for the national teams of Canada, Israel and Poland. Chencinski represented Canada at the 2005 Maccabiah Games. On March 14, 2013, Chencinski received his first call up by the Canadian national team for friendlies against Japan and Belarus. Chencinski made his debut for the national team on March 25 starting the game against Belarus after Milan Borjan was benched following the loss to Japan, the game ended in a 2–0 defeat to the European nation.
Coaching career
In 2013, he was one of the coaches of Maccabi Canada's youth soccer team.
