In 2005, Fichman won the gold medal in women's singles at the 2005 Maccabiah Games in Israel, at the age of 14.

Fichman was inactive from May 2016 to April 2018, but returned to tennis in doubles at the 60k event in Indian Harbour Beach, reaching the quarterfinals with Jamie Loeb.

[7] In 2004, at the age of 13, she was Canada's Under-18 Indoor & Outdoor National girls' champion, and also won the doubles title with partner Mélanie Gloria.

At the 2006 US Open, Fichman reached the quarterfinals in girls' singles and came close to capturing her third major title in doubles with a finalist showing.

She defeated Israeli Julia Glushko in the semifinals[9] and 23-year-old Nicole Ptak of the United States in straight sets in the final.

Fichman reached the 100k Biella Challenger singles final in September 2009, but lost to Petra Martić.

At the WTA Tour Copa Colsanitas, she reached the second round but lost to Catalina Castaño, despite having two match points in the second set.

In July 2012, Fichman won the Waterloo Challenger for the second straight year with a win over Julia Glushko in the championship match.

At the end of January, Fichman won the eighth singles title of her career at the 25k event in Port St. Lucie, with a victory over Tadeja Majerič.

[14] In August, she lost the final of the 100k Vancouver Open to Johanna Konta but won the doubles title alongside Maryna Zanevska.

[15] A week later at the Rogers Cup, she reached the second round for the first time of her career in singles, after defeating compatriot Stéphanie Dubois in her opening match.

She also made it to the semifinals in doubles with fellow Canadian Gabriela Dabrowski by an upset over first seeds Sara Errani and Roberta Vinci.

[16] At the US Open, Fichman qualified for her first-ever Grand Slam main draw with a victory over Alexandra Panova.

[18] In September, Fichman made it to the Premier Mandatory main draw in Beijing with wins over Paula Ormaechea and Yaroslava Shvedova in first and last round of qualifying, respectively.

The same week, she won her first WTA doubles title alongside Maria Sanchez with a victory over Lucie Hradecká and Michaëlla Krajicek in the final.

[22] At the beginning of March, she qualified for the Premier Mandatory Indian Wells Open and defeated Shahar Pe'er in the first round.

[23] In May, Fichman reached her first singles final of the season at the 100k Open de Cagnes-sur-Mer, where she won the biggest tournament of her career so far with a victory over Timea Bacsinszky.

[32] In April 2018, Fichman returned to the pro circuit at age 27, playing in doubles at the 60k event in Indian Harbour Beach.

[5] Partnering with Mexican player Giuliana Olmos, Fichman reached her first Grand Slam tournament quarterfinal at the Australian Open,[33] where they lost to eventual runners-up Barbora Krejčíková and Kateřina Siniaková in three sets.