At the conclusion of the season Gus Kouzmanis was awarded the CSL Golden Boot and David Gee received the Coach of the Year at the CPSL Awards Banquet. For the 1999 season Gee signed Canadian international Elvis Thomas and Phil Caporella from the Montreal Impact. The 1999 season was a repeat of the previous year with Toronto recapturing the regular season championship once more while making history by becoming the first club in the CPSL to go undefeated two seasons in a row. Four of Toronto's players led the scoring charts with Berdusco leading while Kouzmanis, Thomas, and Matas taking the rest of the top four positions. The club finished once more with the best offensive and defensive record in the league. The Olympians defended their Open Canada Cup title successfully by defeating Toronto Croatia by a score of 3–0. They would face Toronto Croatia again this time in the playoff final where the Olympians would mark another milestone in CPSL history by becoming the first club to win a treble within the league. The match resulted in a 2–0 victory with goals from Thomas and Handsor, the attainment established the Scarborough side as a powerhouse within the league. At the CPSL Awards Banquet the Toronto Olympians received four awards – the organization received the Fair Play Award, David Gee for the second year in a row received the Coach of the Year, Elvis Thomas received the Canadian Soccer League MVP Award and Eddy Berdusco won the CPSL Golden Boot. While Elvis Thomas made history by holding the distinction of being first CPSL player to be called up for the Canadian national soccer team, while playing in the league.