Rogowska started her professional career on the ITF circuit at age 14, losing in the first round of qualifying at a $25,000 tournament in Mount Gambier. At the age of 15 she won her first ITF main draw match at a $25,000 tournament in Melbourne. She had a disappointing 2007 season with a 3 wins to 9 loss record. Her fortunes picked up in 2008 making her first professional career quarterfinal in a $25,000 tournament in Berri after qualifying. She then made her first semifinal in a $10,000 tournament in Budapest. Rogowska found some good form late in 2008, playing a $25,000 tournament in Traralgon. She qualified and then made the quarterfinals. Her final tournament of the year was a $25,000 tournament in Sorrento, Australia. Rogowska broke through and won her first professional tournament at the age of 17. She won the tournament with the loss of only 1 set.
She received a wild card into the 2009 Australian Open where she lost in the 1st round to the 31st seed Alona Bondarenko, 7–5, 3–6, 2–6.
She then received a wildcard into the 2009 French Open and defeated Maria Kirilenko in the first round in straight sets 6–4,6–4. In the second round she lost to Kateryna Bondarenko 4–6,7–5,7–5.
After gaining another wild card entry into the 2009 U.S. Open, Olivia almost caused a major upset in her first round match, taking world number 1 and top seed Dinara Safina to three sets. She won the first set 7–6 in a tie breaker and lead 3–0 in the final set before Rogowska's nerves set in and Safina made her comeback losing 7–6, 2–6, 4–6.
At the wild cards for the 2010 Australian Open Rogowska barely made the quarterfinal rounds by losing 2 out of 3 matches in the round robin stage, she only made it through by one game. In the Quarter and Semi finals Rogowska beat Monika Wejnert and Jessica Moore in straight sets, in the final Rogowska lead Casey Dellacqua 6–1, 5–2 and held three match points before Dellacqua came back to win 1–6, 7–6, 6–3.
Rogowska played her first tournament in the 2010 Brisbane International defeating Anastasia Yakimova in the first qualifying round, before losing to Evgenia Rodina. That began an 11 match losing streak, including a 3 set loss to Sorana Cirstea at the Australian Open.
She ended her losing streak in May reaching the quarterfinals of $50,000+H Saint-Gaudens, losing to Kaia Kanepi. She continued to find moderate success in ITF challengers, while losing her first qualifying matches at the French Open, Wimbledon and the US Open.
Rogowska found form late in the year, winning the $25,000 Cairns doubles title, then the $25,000 Darwin singles title, followed by a semifinal at the $25,000 event in Alice Springs. She is now representing Australia at the 2010 Commonwealth Games, reaching the semifinals in singles where she lost to India's Sania Mirza 1–6 6–4 6–4, meaning she was relegated to the Bronze medal playoff where she lost to compatriot Sally Peers. She also made the doubles final with Jessica Moore and will play for the gold medal. Rogowska and Moore lost the final to Anastasia Rodionova and Sally Peers 6–3 2–6 6–3.
Her last tournament of the year was the Australian open wildcard playoff. In the round robin stage she won her first match against Belinda Woolcock 6–3 6–3, she then defeated Azra Hadzic 6–1 6–3 and in her final round robin match she defeated her Commenwealth games doubles partner Jessica Moore 7–6 6–3. She then was drawn to face Sophie Ferguson for a place in the final and Rogowska defeated Ferguson 7–6 6–4. She came back from 1–6 1–3 down in the final against Jelena Dokic to win 1–6 7–6 6–3 to win a wildcard into the 2011 Australian open.
Rogowska started her year at the qualifying draw at the 2011 Brisbane International. In the first round of qualifying she defeated world number 90 Shuai Zhang 6–0 4–6 6–1. She lost the second round to world number 139 Arantxa Rus 6–1 6–7 6–2. At the 2011 Moorilla Hobart International maindraw Rogowska lost to Tamira Pazek 6–1 6–3. In the 2011 Australian Open first round Rogowska lost to Evgeniya Rodina 6–3 6–1.
Rogowska then played the $25,000 Burnie International where she lost in the quarterfinals. Up until the end of March Rogowska played in singles and doubles at 4 $25,000 tournaments in Sydney, Mildura, Ipswich and Bunderberg. Rogowska lost early in singles in Sydney and Mildura but in Ipswich she returned to form but lost in the semifinal to Sally Peers 6–3 7–6. Then in Bundaberg Rogowska defeated Sandra Zaniewska, Olga Puchkova, Sacha Jones and Wen-Hsin Wsu before losing the final to Casey Dellacqua 6–2 6–3. Rogowska played with Casey Dellacqua in doubles in all four events and they went on a 16 match winning streak to win those events.
At the 2011 French Open Rogowska lost in the first round of qualifying to world number 163 Regina Kulikova 7–5 6–3. Shen then played a 25,000 event in Grado and made the semifinal defeating Karolina Pliskova 6–4 6–0, Yulia Putintseva 7–5 6–2 and won when Lenka Jurikova 4–1 (n retired) but lost to world number 182 Ajla Tomljanovic 6–0 4–6 6–3. In early July Rogowska played in her first WTA match since the Australian open where she qualified for the 2011 Swedish Open in Bastad where she played world number 21 and second seed Flavia Pennetta and lost 6–2 7–5.
She next played in a $100,000 tournament to warm up for the US Open. She qualified and made the second round. Rogowska lost in the 1st round of qualifying at the 2011 US Open to world number 211 Petra Rampre 7–6(3) 7–5. Rogowska then played 8 $25,000 tournaments to ennd her year on the WTA circuit. She won her first singles tournament of the year in Alice Springs after defeating Abbie Myers, Alison Bai, Tammi Patterson, Akiko Omae and Isabella Holland. Next in Darwin she lost in the semifinals to Casey Dellacqua 6–4 7–6. Rogowska again lost to Dellacqua the next week in Esperance but this time in the final 6–2 6–1. Rogowska's good form continued with a quarterfinal in Kalgoorlie and then winning her second tournament of the year in Port Pirie beating world number 127 Erika Sema 6–3 6–0 in the semi final and compatriot Bojana Bobusic 6–3 6–2 in the final. She then made two consecutive semifinals to end her year on the pro tour, losing to Sacha Jones 7–5 6–2 in Traralgon and Isabella Holland 6–4 6–4 in Bendigo.
Her final tournament of the year was the Australian Open wildcard playoff where she won her pool matches against Azra Hadzic 6–3 6–2, Daniella Jeflea 6–3 7–5 and Belinda Woolcock 6–0 6–4. In her semifinal she defeated Bojana Bobusic 6–4 7–5. She played 15-year-old Ashleigh Barty in the final and things looked good for Rogowska as she led 5–2 in the first set, but Barty came back and took the match 7–6 6–2. Rogowska improved her WTA ranking in 2011 from 259 to 167.
She started her year at the 2012 Brisbane International after receiving a main draw wildcard. She played world number 44 Barbora Zahlavova-Strycova and put up a great fight before going down 6–2 4–6 6–4. She then played the 2012 Moorilla Hobart International qualifying after receiving a wildcard. Rogowska recorded a great win beating world number 69 Alberta Brianti 6–1 6–1 but lost to Heather Watson. After receiving a Wild Card entry into the 2012 Australian Open, Rogowska won her first grand slam main draw match since the 2009 French Open, defeating Sweden's Sofia Arvidsson in straight sets, 6–3 6–1. In the second round Rogowska lost to world number 5 and 2011 finalist Na Li 6–2 6–2.
Rogowska then competed in three $25,000 events in Burnie, Launceston and Sydney. At the Burnie International she was the second seed. She defeated qualifiers Lesly Kerkhove, Su Jeong Jang and Shuko Aoyama in the first round, second round and quarterfinal. In the semifinal she defeated compatriot Bojana Bobusic 6–2 6–4 and in the final she defeated Russian world number 1 junior Irina Khromacheva 6–3 6–3 to win her 6th ITF title. She looked to continue her good form in Launceston but it looked like it was over in the first round before Rogowska made a big comeback to win 1–6 7–5 7–6 over Sandra Zaniewska. She than beat Arina Rodionova but lost the quarterfinal to Yulia Putintseva. In Sydney Rogowska made the final by beating Akiko Omae 6–2 6–0, Monique Adamczak by walkover, Saisai Zheng 6–4 6–1 and qualifier Richel Hogenkamp 3–6 6–0 6–2. In the final she lost to Ashleigh Barty 6–1 6–3.
Olivia then played in the main draw of the BMW Malaysian Open, where she played Elitsa Kotsova in the first round and won 6–4 6–0 which was her third WTA main draw win. She continued her good form into the second round upsetting defending champion Jelena Dokic 3–6 6–4 7–6, making the quarterfinals which is her best WTA event to date. In the quarterfinals she was lost to Eleni Daniilidou 6–2 3–6 6–2 although Rogowska won the second set after a rain delay. Rogowska then had first round losses at the 2012 BNP Paribas Open qualifying to Varvara Lepchenko 6–1 6–3 and then in the main draw of the 2012 Sony Ericsson Open to Stephanie Foretz Gacon 6–4 6–1.
Olivia played Fed Cup for the first time taking on Germany in Germany in the World Group Playoffs. The team also included Samantha Stosur, Jarmila Gajdosova and Casey Dellacqua. Rogowska played in the second of the reverse singles but although pushing world number 14 Angelique Kerber she eventually lost 6–3 6–3. She then had a few disappointing results in ITF tournaments in the USA on red clay. Olivia played her final French open warm up tournament at the premier level tournament the 2012 Brussels Open. Olivia won her first qualifying match over Maryna Zanevska 6–4 2–6 7–5 but lost her second round to Lenka Wienerova 6–4 5–7 6–4. Olivia then had a bad patch with a first round qualifying defeat at the 2012 French Open then two disappointing results on grass. Then Olivia lost in the second round of Wimbledon qualifying. She had some encouraging results in the American Hard court season which finished with a first round loss at the 2012 US Open to Mandy Minella 6–2 3–6 6–3.
After months away Olivia returned home to Australia to play a string of $25,000 tournaments across the country. Her first one was in Rockhampton where she made the final with 4 straight set wins. Although having a tough start she came back to defeat Sacha Jones 0–6 6–3 6–2 to win the tournament. The next week in Port Pirie she lost in the final to Jones who hadn't lost a set all week 6–2 7–5. Two weeks later in her next $25,000 tournament in Esperance she only lost 1 set all week and played a great final to defeat Ashleigh Barty 6–0 6–3. She lost to Barty in a final in Sydney earlier in the year by nearly the same score.
Due to big ranking improvements in 2012, Rogowska was awarded wildcards into the 2013 Brisbane International, 2013 Apia International Sydney and the 2013 Australian Open. In Brisbane, Rogowska drew qualifier Monica Puig and lost in straight sets. Rogowska was drawnt to play world number 13 Maria Kirilenko in Sydney. Rogowska made a career breakthrough in 2009 after defeating Kirilenko at the 2009 French Open. After a close first set, Rogowska eventually lost in straight sets. At the 2013 Australian Open, Rogowska played qualifier Vesna Dolonc. Rogowska was defeated in an extremely close three set match where she lost 6–8 in the final set.
Rogowska then headed to Burnie to defend the title she won in 2012 at the $25,000 2013 McDonald's Burnie International. As the top seed, she defeated Camilla Rosatello, Misa Eguchi, Arina Rodionova and Bojana Bobusic all in straight sets. In a windy final, she played Monique Adamczak and won a thriller 7–6(5), 6–7(7), 6–4. Staying in Tasmania, Rogowska made the quarterfinals of a $25,000 tournament in Launceston. But was stunned by eventual champion Storm Sanders in two close sets.
Rogowska then competed in qualifying at the 2013 Dubai Tennis Championships where she defeated Fatma Al Nabhani in straight sets. She was crushed in the second round by world number 28 Carla Suarez Navarro. Rogowska was given direct entry into the WTA event, the 2013 Malaysian Open where she lost in the first round against qualifier Luksika Kumkhum.
Rogowska then started to prepare for the French Open by playing six ITF events in Australia, Thailand, Slovak Republic and Czech Republic. Her best result coming in a $25,000 event in Bundaberg where she reached the quarterfinals going down to Yurika Sema in three sets. Her final tournament before the French Open was at the 2013 Brussels Open where she won her first round of qualifying against Valeria Solovyeva in straight sets. She then lost in two close sets against fourth seed Coco Vandeweghe. At the 2013 French Open Rogowska competed in qualifying where again defeated Valeria Solovyeva in straight sets. in the next round she lost to fellow Australian and number 20 seed Anastasia Rodionova.
Rogowska competed in qualifying at the 2013 US Open (tennis) where she upset eighth Johanna Konta. She then defeated Richel Hogenkamp in three close sets. She lost in the final round of qualifying against Maria Joao Koehler. However Rogowska was awarded a lucky-loser place in the main draw after Ayumi Morita had to withdraw with a lower back injury. In the first round she was defeated 0–6, 0–6 by fourth seed Sara Errani.
Rogowska began her year at the 2014 Brisbane International after receiving a wildcard. She lost in the first round to Kimiko Date-Krumm. Rogowska then competed at the 2014 Hobart International after being awarded a wildcard. She opened with a straight sets win over world number 59 Alexandra Cadantu. In the second round, Rogowska won the first set over eighth seed Bojana Jovanovski before she came storming back to easily win the next two sets. On 8 January, Rogowska was awarded a wild card into the 2014 Australian Open. Rogowska won her first round over Mariana Duque in straight sets. This was Rogowska's third Grand Slam first round win. In the 2nd round, she lost to Elina Svitolina.
Olivia returned to the ITF circuit in Australia, playing two $50,000 events in Tasmania. She won the 2nd event in Launceston, defeating Irena Pavlovic in the final. It was her first title at the $50,000 level and the biggest of her career to date. She also won the doubles title with partner Monique Adamczak, propelling her to a career-high doubles ranking of 106.