Toskala turned heads with his stellar play in the 1998–99 season with Ilves of the Finnish SM-liiga, where he went 21–12–0 with a 2.14 goals against average, a 0.916 save percentage and five shutouts.

Toskala considered quitting hockey to attend school full-time, until the San Jose Sharks enticed him to North America.

The next year, after the team's move to Cleveland, he took over the starting role after Kiprusoff was recalled to the San Jose Sharks, and in 62 games, he went 19–33–7 with a 2.99 GAA and a 0.912 save percentage.

When Kiprusoff fell to injury, Toskala was called up to San Jose to serve as back-up to regular starter Evgeni Nabokov.

In the 2002–03 NHL season, after Evgeni Nabokov and the Sharks could not settle on a contract, Toskala served as Kiprusoff's backup.

After Nabokov was re-signed, however, Toskala was sent back to the Sharks' minor league affiliate in Cleveland, where he struggled, going 15–30–2 with a 3.21 GAA and a 0.903 save percentage.

He began as the backup to Evgeni Nabokov, but after a start on February 8, he posted a record of 17–2–2, leading the team to a playoff berth.

He and goaltender Andrew Raycroft shared starts until late November, when Toskala's GAA and save percentage improved dramatically.

On a Leafs power play, defenceman Rob Davison of the Islanders attempted to clear the puck out of his defensive zone.

[4] For the first game of the following season, on October 1, 2009, Toskala was the Maple Leafs starting goaltender in an overtime loss to the Montreal Canadiens.

In late 2009, a prank he pulled on interviewer Zdenek Matejovsky received coverage from Finnish news and 424 000 views on YouTube (note: the original video was removed).

On November 1, 2010, due to AIK IF of the Elitserien (SEL) suffering from injuries, Toskala signed a one-month contract with the club.