He played as a goalkeeper for several clubs in the United States and Canada, namely Vermont Voltage, Montreal Impact, Laval Dynamites and Trois-Rivieres Attack.

From 1999 he went on to play college soccer with Southern Connecticut State University, where he was a four-year starter and named into the conference and region all-star teams each year.

Throughout his time with Montreal he mostly played as a back-up for Greg Sutton, which led him to sign with the Laval Dynamites of the Canadian Soccer League.

[16] Between September 2003 and March 2004, he enjoyed his best moments with the Canada's U23 national team while taking part in the 2004 CONCACAF Men's Pre-Olympic Tournament.

As Canada's first choice goalkeeper, he helped the canucks through the preliminary rounds, beating the US Virgin Islands and El Salvador in a home and away series.

The ladder requiring an exciting return leg where Canada won 1-0 to tie the aggregate score and then secured a trip to Guadalajara, Mexico through a shootout.

[17] Although Canada did not secure a spot in the 2004 Summer Olympics, Olivieri shined in the final round of qualifying and was honored on the tournament all-star team.

During his time with ARS Lac St-Louis, Olivieri also served on a number of Quebec Provincial Team staff's in a variety of technical roles from assistant to goalkeeper coach.

In January 2012, the Canadian Soccer Association officially hired Olivieri as the Women's Excel Director for national team players between the ages of 18 and 23.