5 Best Soccer Players from Toronto, Ranked

Many Toronto-born soccer players enjoyed glimmering professional careers, several of whom helped Canada win the 2000 Gold Cup against all odds. That victory was Canada’s soccer version of the Miracle on Ice. 

But who is the best and most influential Toronto-born soccer player? 

I feature the headline act while covering the top five. 

5 Best Soccer Players from Toronto, Ranked

Greatest Soccer Players from Toronto

1. Paul Stalteri

Paul Stalteri was one of the first players to put Canada on the soccer map, thanks to his exploits in Germany and England. The rugged, rough-and-tumble right-back collected some silverware in his decorated career, winning the Bundesliga with Werder Bremen in 2003-04. 

While that was his most impressive success at the club level, Stalteri famously led Canada to the 2000 Gold Cup victory, a tournament in which Canada were the massive soccer betting underdogs. 

Canada beat Colombia 2-0 in the final. Stalteri won the English League Cup with Tottenham in 2008, the last time that club had won any silverware before claiming the 2025 Europa League. 

2. Dwayne De Rosario 

Dwayne De Rosario, the MLS journeyman, played for five MLS teams during a career that spanned two decades. He also briefly plied his trade in Europe, making 12 Bundesliga appearances for FSV Zwickau during the 1997-98 season.

He was another instrumental factor in Canada’s 2000 Gold Cup success. De Rosario won four MLS Cups and was named the MLS MVP for the 2010-11 season. He played in five Gold Cups and made 80 appearances for the Canadian national team. 

3. Jonathan Osorio

As improbable as it is admirable, Jonathan Osorio has spent his entire 15-year career with one club, Toronto FC. He’s scored 67 goals while adding 38 assists in 385 appearances for the first club to break into the MLS market. 

Rewarded for his unbridled loyalty, Osorio helped lead Toronto FC to their first MLS Cup in 2016-17. He’s also made 85 appearances for the Canadian national team. 

4. Jim Brennan 

Jim Brennan broke onto the scene the same year that Stalteri did, following a similar path. Brennan played for five English teams before spending the twilight of his career, from 2007 to 2010, with Toronto FC. 

Alongside De Rosario and Stalteri, Brennan shocked the soccer world in North America by helping Canada win the 2000 Gold Cup. 

5. Julian de Guzman

Julian de Guzman made his rounds during his 17-year career, playing for eight clubs in six countries. His most high-profile tenures came in Spain with Deportivo de La Coruna and in Germany with Hannover 96. 

He made 97 La Liga and 78 Bundesliga appearances. He also made 93 appearances with his hometown team, Toronto FC. 

The biggest blight on de Guzman’s career was his lack of silverware. He won three Canadian Cups with Toronto and secured the Saarland Cup with FC Saarbrucken. 

Who Is the Best Soccer Player Born in Toronto?

Stalteri is the best soccer player born in Toronto. 

While many players have followed in his footsteps, Stalteri was one of the most influential homegrown players to expose Canadian soccer to the rest of the world. 

He also played an integral role in helping Werder Bremen win the Bundesliga and Canada the Gold Cup.