Rogowska started her professional career on the ITF Circuit at age 14, losing in the first round of qualifying at a $25k tournament in Mount Gambier. At the age of 15, she won her first main-draw match at a $25k tournament in Melbourne.
She had a disappointing 2007 season with a win–loss record of 3–9.
Her fortunes picked up in 2008 making her first career quarterfinal in a $25k tournament in Berri after qualifying. She then made her first semifinal in a $10k tournament in Budapest. Late in 2008, at a $25k event in Traralgon, Rogowska qualified and then made the quarterfinals. Her final tournament of the year was a $25k tournament in Sorrento, Australia. Rogowska broke through and won her first professional tournament at the age of 17– with the loss of only one set.
2009
She received a wildcard into the Australian Open where she lost in the first round to the 31st seed Alona Bondarenko in a three-set match.[3] She then received a wildcard into the French Open and defeated Maria Kirilenko in the first round in straight sets. In the second round, she lost to Kateryna Bondarenko in three sets.[3]
After gaining another wildcard entry into the US Open, Olivia almost caused a major upset in her first-round match, taking world No. 1 and top seed Dinara Safina to three sets. She won the first set in a tie breaker and led 3–0 in the final set before her nerves set in and Safina made her comeback, losing 7–6, 2–6, 4–6. At the Wildcard Playoff for the 2010 Australian Open, Rogowska barely made the quarterfinal rounds by losing two out of three matches in the round-robin stage; she only made it through by one game. In the quarterfinals and semifinals 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.
2010
Rogowska played her first tournament in the Brisbane International defeating Anastasia Yakimova in the first qualifying round, before losing to Evgeniya Rodina. That began an 11-match losing streak, including a three-set loss to Sorana Cîrstea at the Australian Open.
She ended her losing streak in May reaching the quarterfinals of $50k+H Saint-Gaudens, losing to Kaia Kanepi, and continued to find moderate success in ITF events, while losing her first qualifying matches at the French Open, Wimbledon and the US Open.
Rogowska found form late in the year, winning the $25k Cairns doubles title, then the $25k Darwin singles title, followed by a semifinal at the $25k event in Alice Springs. She represented Australia at the 2010 Commonwealth Games, reaching the semifinals in singles where she lost to India's Sania Mirza 6–1, 4–6, 4–6, 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 to play for the gold medal but Rogowska and Moore lost the final to Anastasia Rodionova and Sally Peers, in three sets.
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 her Commonwealth 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 Dokić to win 1–6, 7–6, 6–3 to win a wildcard into the main draw of the 2011 Australian Open.
Rogowska then played the $25k Burnie International where she was eliminated in the quarterfinals. Up until the end of March, she played in singles and doubles at four $25k tournaments in Sydney, Mildura, Ipswich and Bunderberg. She lost early in singles in Sydney and Mildura but in Ipswich she returned to form but lost in the semifinal to Sally Peers 3–6, 6–7. Then in Bundaberg, Rogowska defeated Sandra Zaniewska, Olga Puchkova, Sacha Jones and Wsu Wen-hsin, before losing the final to Casey Dellacqua 2–6, 3–6. She played with Dellacqua in doubles in all four events and they went on a 16-match winning streak to win those events.
At the French Open, Rogowska lost in the first round of qualifying to world No. 163, Regina Kulikova, 5–7, 3–6. Shen then played a $25k event in Grado and made the semifinal defeating Karolína Plíšková 6–4, 6–0, Yulia Putintseva 7–5, 6–2 and won when Lenka Juriková retired but lost to world No. 182, Ajla Tomljanović, 0–6, 6–4, 3–6. In early July, Rogowska played in her first match on WTA Tour since the Australian Open and qualified for the Swedish Open in Båstad where she played world No. 21 and second seed, Flavia Pennetta, and lost 2–6, 5–7.
She next played in a $100k tournament to warm-up for the US Open. She qualified and made the second round. Rogowska lost in the first round of qualifying at the US Open to world No. 211, Petra Rampre, 6–7, 5–7. She then played eight $25k tournaments to end her year on the WTA Tour. 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 4–6, 6–7. Rogowska again lost to Dellacqua the next week in Esperance but this time in the final 2–6, 1–6. Her good form continued with a quarterfinal in Kalgoorlie and then winning her second tournament of the year in Port Pirie beating world No. 127, Erika Sema, 6–3, 6–0 in the semifinal, 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 5–7, 2–6 in Traralgon, and Isabella Holland, 4–6, 4–6 in Bendigo.
Her final tournament of the year was the Australian Open Wildcard Playoff where she won her pool matches against Azra Hadzic, Daniella Jeflea and Belinda Woolcock. 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.
2012
She started her year at the Brisbane International, after receiving a main-draw wildcard. She played world No. 44 Barbora Záhlavová-Strýcová and put up a great fight before going down 2–6, 6–4, 4–6. She then played the Hobart International qualifying after receiving a wild card. Rogowska recorded a great win beating world No. 69, Alberta Brianti, 6–1, 6–1 but lost to Heather Watson. After receiving a wildcard entry into the Australian Open, Rogowska won her first Grand Slam main-draw match since the 2009 French Open, defeating Sofia Arvidsson in straight sets, 6–3, 6–1. In the second round, Rogowska lost to world No. 5 and 2011 finalist, Li Na, 2–6, 2–6.
Rogowska then competed in three $25k events in Burnie, Launceston and Sydney. At the Burnie International, she was the second seed. She defeated qualifiers Lesly Kerkhove, Jang Su-jeong 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-one junior Irina Khromacheva 6–3, 6–3 to win her sixth ITF title. In Launceston, her good form looked like it was over in the first round before Rogowska's comeback to win 1–6, 7–5, 7–6 over Sandra Zaniewska. She then 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, Zheng Saisai 6–4, 6–1 and qualifier Richèl Hogenkamp 3–6, 6–0, 6–2. In the final, she lost to Ashleigh Barty in straight sets.
In the main draw of the Malaysian Open, she won in the first round against Elitsa Kotsova 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 Dokić 3–6, 6–4, 7–6, making the quarterfinals. In the quarterfinals, she lost to Eleni Daniilidou 2–6, 6–3, 2–6 although Rogowska won the second set after a rain delay. Rogowska then had first-round losses at the Indian Wells Open qualifying to Varvara Lepchenko 1–6, 3–6, and then in the main draw of the Miami Open to Stéphanie Foretz Gacon 4–6, 1–6.
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 Gajdošová and Casey Dellacqua. Rogowska played in the second of the reverse singles but although pushing world No. 14, Angelique Kerber, she eventually lost 3–6, 3–6. 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 Brussels Open. She won her first qualifying match over Maryna Zanevska 6–4, 2–6, 7–5 but lost her second round to Lenka Wienerová 4–6, 7–5, 4–6. Olivia then had a bad patch with a first-round qualifying defeat at the 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 hardcourt season, including the US Open where she was initially placed in the qualifiers, but when she was receiving a wildcard to the main draw after Dellacqua promoted to the last direct entry list just as qualifying matches was to be started. She finished with a first round loss to Mandy Minella, 2–6, 6–3, 3–6.
After months away, Olivia returned home to Australia to play a string of $25k tournaments across the country. Her first one was in Rockhampton where she made the final with four straight-sets 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, South Australia, she lost in the final to Jones who hadn't lost a set all week 2–6, 5–7. Two weeks later in her next $25k tournament in Esperance, she only lost one 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.
2013
Due to big ranking improvements in 2012, Rogowska was awarded wildcards in Brisbane, Sydney and the Melbourne.
In Brisbane, Rogowska drew qualifier Monica Puig and lost in straight sets.
She was drawn to play world No. 13, Maria Kirilenko in Sydney. After a close first set, Rogowska eventually lost in straight sets. At the Australian Open, Rogowska played qualifier Vesna Dolonc but 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 $25k 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, 6–7, 6–4. Staying in Tasmania, Rogowska made the quarterfinals of a $25k tournament in Launceston. But was stunned by eventual champion Storm Sanders in two close sets.
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 $25k 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 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 French Open, Rogowska competed in qualifying where again defeated Solovyeva in straight sets. In the next round, she lost to fellow Australian and No. 20 seed Anastasia Rodionova.
Rogowska competed in qualifying at the US Open where she upset eighth seed Johanna Konta. She then defeated Richèl Hogenkamp in three close sets. She lost in the final round of qualifying against Maria João Koehler. However, Rogowska was awarded a lucky-loser place in the main draw after Ayumi Morita had to withdraw with a back injury. In the first round, she was defeated 6–0, 6–0 by fourth seed Sara Errani.[4]
2014
Rogowska began her year at the Brisbane International after receiving a wild card.[5] She lost in the first round to Kimiko Date-Krumm.[6] Rogowska then competed at the Hobart International, after being awarded a wildcard.[7] She opened with a straight sets win over world No. 59, Alexandra Cadanțu.[8] 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.[9] On 8 January, Rogowska was awarded a wildcard into the Australian Open.[10] Rogowska won her first-round match over Mariana Duque in straight sets. This was her third Grand Slam first-round win.[11] In the second round, she lost to Elina Svitolina.
Olivia returned to the ITF Circuit in Australia, playing two $50k events in Tasmania. She won the second event in Launceston, defeating Irena Pavlovic in the final. It was her first title at the $50k-level and the biggest of her career to date. She also won the doubles title with partner Adamczak, propelling her to a career-high doubles ranking of 106.