Chapleski is a native of Broomfield, Colorado who grew up playing for Broomfield High School and the Colorado Rush Academy. At Broomfield, he won a state championship in 2007 in which the team posted an undefeated record of 20-0 and he was named the team offensive MVP. In 2009 he was named the Gatorade Colorado Player of the Year as well as an NSCAA All American. His Colorado Rush Academy team spent much of its time ranked in the top 10 in the country and beat out various U17 national teams to win a World Youth Tournament in 2009
During his time as a prep athlete, Chapleski was also a 2-time Adidas ESP all star selection, being lucky enough to share the field with all-star game guest player, Zinedine Zidane. After his time at Broomfield and Colorado Rush, he went on to play collegiately for 4 years at the University of Denver. A regular starter, senior team captain and first team all-conference selection, Chapleski helped guide the Pioneers to a Summit League championship and two appearances to the NCAA tournament. The 2013 team his senior year set numerous program records for wins, goals and shutouts.
After his time as a player concluded, Chapleski went straight into working on the other side of the sideline, first serving as the Director of Operations at his alma matter DU, helping guide the team to yet another conference title. He then moved into the club space where he served as a staff coach and the Director of Player Development at Colorado Rush, later on as a staff coach again at Colorado Rapids Youth.
Upon the conclusion of years working in the club game, Chapleski went back into the college ranks, first as a graduate assistant coach at Regis University where he simultaneously guided the team to the RMAC tournament championship game and obtained his Master’s Degree in Organizational Leadership before arriving at his current post as an assistant coach at another top RMAC program, MSU Denver. Chapleski also serves as the General Manager at Let’s Play Soccer Northglenn, an indoor soccer Facility in the Northglenn area.