01/22/2014 21:36 EST | Updated 03/24/2014 05:59 EDT

Eugenie Bouchard down 1 set at Australian Open 2014

Eugenie Bouchard's Australian Open semifinal quest hasn't gotten off to the start she had hoped for.

The Montreal native fell 2-6 in the opening set to No. 4 seed Li Na of China, after falling behind 0-5 and struggling at the start. The 19-year-old is trying to become the first Canadian to advance to a Grand Slam singles final in the process.

They're currently playing the second set in Melbourne.

With a 5-7, 7-5, 6-2 quarter-final win over No. 14 seed Ana Ivanovic on Tuesday (in Australian time), Bouchard became the first Canadian in nearly 30 years to get that far in a Grand Slam (Carling Bassett was the last at the 1984 U.S. Open).  

Na, a former French Open champion, ousted Flavia Pennetta of Italy 6-2, 6-2 to earn a berth in the semifinals.

Montreal-born players Greg Rusedski and Mary Pierce also have had some deep runs, but both were representing different countries. Rusedski was competing for Great Britain when he made the U.S. Open final in 1997, while Pierce's two major titles came while representing France.