Canada carried out its first air strikes in Syria on Wednesday the military said, according to AFP.
The move is part of Ottawa's plans to expand its contribution to the US-led coalition against Islamic State, after parliament approved a larger role in the conflict.
Two F-18s using precision-guided munitions struck a ISIS position near the Syrian city of Raqqa, before safely returning to base, the military announced.
The strike near Raqqa, an ISIS stronghold, was carried out with a group of 10 aircrafts, including six US planes.
Canadian strikes had been limited to Iraqi territory, but at the end of March Canadian lawmakers narrowly passed a measure to allow the country's aircraft to target ISIS targets in Syria.
Opposition lawmakers argued Canada should not deepen its involvement in the long-running and complex war.
Canada first joined the anti-ISIS coalition in November and it has also deployed about 70 special forces troops to train Kurds to fight ISIS in northern Iraq.
Despite a sustained air campaign and ground advances in Iraq, the radical group still holds large swaths of territory straddling Syria and Iraq.