Born on 10 January 1986 in Geel, Belgium as the only child of a car dealer and a house wife. She began playing tennis at 4 years old. Flipkens played tennis, football, volleyball and basketball before eventually deciding to pursue a career as a tennis player at the age of 12. She then went to the tennis academy in Wilrijk where she became friends with Kim Clijsters. At the age of 17, after winning Wimbledon and the US Open as a junior, she dropped out of school to continue her career as a professional tennis player. She speaks Dutch, English, French and German. One of her trademarks are her prescripted glasses, which she has to wear since she's myopic.
In 2001, Flipkens won the bronze medal at the European Youth Olympics Festival in Murcia, Spain.
In 2002, Flipkens and Elke Clijsters won the girls' US Open doubles title, beating Shadisha Robsinon and Tory Zawacki in the final with 6–1, 6–3.
In 2003, Flipkens won the Wimbledon Championships in Girls' Singles beating Anna Chakvetadze 6–4, 3–6, 6–3 and the US Open in girls' singles, defeating Michaëlla Krajicek, 6–3, 7–5. Following her two wins in two Grand Slam juniors events, Flipkens was selected to join the Belgium Fed Cup team for the 2003 Fed Cup's semifinal opposing the United States. She played her first Fed Cup match against then WTA no. 17 Meghann Shaughnessy and lost 7–6 (7/4), 6–7 (8/10), 7–9. She finished 2003 as World no. 1 in both singles and doubles on the junior rankings. At the end of the year, she received the award for Best Belgian Talent and was named ITF Junior World Champion.
Flipkens played her first professional match in 2001, but didn't officially become a professional tennis player until 2003. She won her 2nd ITF title in Innsbruck, Austria in July 2004 but then struggled with a congenital back injury during the second half of 2004, causing her to be unable to play for several months. In August 2005, she won her 3rd ITF title in Hechingen, Germany. In October 2005, Flipkens won her first main draw match on a WTA tournament in Hasselt, against Italian Silvia Farina Elia. At the 2006 French Open, Flipkens qualified for the main draw of a Grand Slam for the first time in her career. She reached the second round. In Wimbledon 2006, Flipkens reached the main draw of a Grand Slam for the second time. She lost to Jamea Jackson in the first round. She partnered then British no. 2 Andy Murray in mixed doubles. She also reached the second round in the 2006 US Open after qualifying, falling to eventual semifinalist Jelena Janković. In September 2006, she replaced the injured Kim Clijsters as the second member of the Belgian Fed Cup team in the final against Italy, alongside Justine Henin-Hardenne. Flipkens lost both her singles matches (against Schiavone and Santangelo). She and Henin-Hardenne then played the decisive doubles together, but had to retire in the third and final set due to Henin-Hardenne tearing a muscle in her leg, which led to Belgium losing the final with 3–2. In 2007, Flipkens suffered from an injury to the wrist, which resulted in her not being able to play for several months. In 2008, she reached the second round of WTA Estoril, beating Lucie Šafářová with 7–5, 6–4 in the first round. She also won three ITF tournaments in 2008.
In 2009, Flipkens reached the second round of the Australian Open and the French Open. She defeated no. 30 Ágnes Szávay in order to reach the second round at Wimbledon, where she faced Elena Baltacha. Flipkens beat the British wildcard in straight sets to set up an encounter with top seed Dinara Safina and a place in a Grand Slam third round for the first time in her career. She lost to the Russian, after having a set point in the first set, 5–7, 1–6. At the 2009 US Open, she reached the third round, after victories in straight sets over Jelena Dokic and Anabel Medina Garrigues. She suffered a defeat in the third round, losing to compatriot and eventual champion Kim Clijsters, 0–6, 2–6. In October 2009, she again defeated Garrigues to reach the quarterfinals of the Luxembourg Open. After the Australian Open 2009, Flipkens reached the top 100 for the first time in her career at the end of 2009.
At her next Grand Slam, the 2010 Australian Open, Flipkens lost in the first round to another unseeded countrywoman making a comeback, Justine Henin, 4–6, 3–6. At the 2010 French Open, she beat Japan's Ayumi Morita in the first round, 6–1, 6–4. Maria Sharapova beat her in straight sets in the second round. In the week before Wimbledon, she reached the semifinals of the UNICEF Open, a WTA tournament on grass at Rosmalen, where she lost to Andrea Petkovic. At Wimbledon 2010, she lost in the second round to Yanina Wickmayer. She had been troubled by a recurring wrist injury and underwent surgery at the end of the 2010 season.
Flipkens started 2011 with a first-round loss at the Australian Open and did not win one Grand Slam match that year. She reached the semifinals at the 2011 Grand Prix SAR La Princesse Lalla Meryem in Fes, Morocco, during the clay-court season. At Rosmalen, she teamed up with Coco Vandeweghe to reach the semifinals in doubles.
In April 2012, doctors discovered four life-threatening blood clots in her calf, which prevented her from playing for two months. During this time, her ranking dropped to no. 262 and she lost her funding from the Flemish Tennis Association (VTV). She returned to the tour at Rosmalen, where she beat Samantha Stosur in the first round and reached the semi-finals.
She qualified in singles for the 2012 US Open and made it to the second round, where she was defeated by eventual finalist Victoria Azarenka. She also partnered with Kim Clijsters in doubles, but they were beaten in the first round. In September 2012, she won the Bell Challenge in Quebec for her first WTA title, after wins over top-seeded Dominika Cibulková, Mona Barthel and Lucie Hradecká, among others.
In October, she participated in the Generali Ladies Linz tournament, where she won through qualifying and got onto the main draw. She then defeated Alizé Cornet in the first round, a qualifier in the second round, and 2nd seed Ana Ivanovic 6–4, 6–0 in the quarterfinals. Ultimately, she lost in three sets to Julia Görges in the semifinals. This result brought her to a career-high 58th position on the WTA rankings. During this month, Kim Clijsters announced that she would help her as a part-coach. In December 2012, Maxime Braeckman became her new coach full-time coach, but she still occasionally worked with Clijsters.
At the end of the season, she was nominated for "Comeback Player of the Year" at the WTA Awards, an award that would eventually go to Yaroslava Shvedova. In December, Flipkens received the VTV Award for "Belgian Player of the Year".
Flipkens started her 2013 season at the Moorilla Hobart International. In the first round, she won against Francesca Schiavone 2–6, 6–3, 7–6 (7/3) and continued with wins over Bojana Jovanovski and Monica Niculescu, before falling to Mona Barthel in the semifinals (4–6, 4–6). Her next tournament was the first Grand Slam of the year, the Australian Open. She defeated Mandy Minella, Klara Zakopalová, and Valeria Savinykh in the first rounds to advance to the fourth round where she lost 1–6, 0–6 to Maria Sharapova.
She then proceeded to reach the quarterfinal of Memphis (lost to Magdaléna Rybáriková) as well as the quarterfinal of Miami, where she beat Petra Kvitová in the second round before eventually falling to Agnieszka Radwańska. She started the French Open 2013 as 21st seed, and beat Flavia Pennetta in the first round before losing to 2010-champion Francesca Schiavone. After the French Open, Flipkens reached top 20 for the first time.
To prepare for Wimbledon, Flipkens participated in the Aegon Classic in Birmingham. Top-seeded of the tournament, she was free from the first round. In the second round, she beat qualifier Ajla Tomljanovic 4–6, 6–4, 7–5. She lost 7–6 (5), 6–2 to Magdaléna Rybáriková in the third round. A week later, Flipkens was at the Topshelf Open in 's-Hertogenbosch, Netherlands. She advanced to the final but was ultimately beaten by Simona Halep.
Flipkens played at Wimbledon as the 20th seed having not even played in the qualifiers the previous year due to her low ranking. She exceeded expectations by advancing to the semifinals of a Grand Slam for the first time in her career, beating Flavia Pennetta in the fourth round with 7–6, 6–3 and former champion Petra Kvitová with 4–6, 6–3, 6–4 in the quarterfinals. However, she was defeated 1–6, 2–6 by eventual champion Marion Bartoli in the semi-final. During the semifinal, Flipkens suffered from a knee-injury, after which she didn't play for a month.
She reached a career high of 13th in the world on 5 August 2013.
In the first round of Toronto, she beat Venus Williams 0–6, 6–4, 6–2 and reached the quarterfinal before losing to world no. 1 and Venus' sister Serena Williams 0–6, 3–6.
She began the US Open as 12th seed. However, she was beaten in straight sets in the first round by two-time champion Venus Williams, who took revenge for her loss against Flipkens two weeks earlier in Toronto.
In October, it was announced that Flipkens would stop working with Maxime Braeckman due to Braeckman wanting to stay more at home with his family.
Flipkens reached another quarterfinal in Linz and finished the year as 20th in the world. In December, she took part in the Kim Clijsters Invitational, an exhibition tournament where she won against Ana Ivanovic in a singles match and lost against Kim Clijsters and Xavier Malisse, whilst partnering Henri Leconte in a mixed doubles match.
On 22 December 2013, she received the prestigious award for Sportswoman of the Year in Belgium as well as the VTV Award for "Belgian Player of the Year" for the second year in a row.
Flipkens began 2014 by reaching a semifinal in Auckland, where she lost to Ana Ivanovic, 0–6, 6–7. The next week, she reached the quarterfinal of Hobart (losing to Garbiñe Muguruza). She then beat Laura Robson in the Australian Open 2014, where she ended up reaching the second round in which she was defeated by Casey Dellacqua.
In February, she made it into the quarterfinal of Paris, but lost to Maria Sharapova. In Miami, she reached the fourth round before losing to Sharapova again.
In May, Flipkens announced that she would begin to work with ex-tennis player Xavier Malisse. However, their cooperation ended in June, after the French Open, because it didn't work out.
In the French Open, Flipkens lost in the second round to Julia Glushko. Flipkens withdrew from the second round in doubles, with Dominika Cibulková, after she'd fainted on court during training and doctors at the site had sent her to the hospital where she'd spent the night on intensive care since heart problems were feared. However, later tests revealed that she was healthy and fit to play.
Flipkens reached the quarterfinal of Birmingham, where she was beaten by Barbora Záhlavová-Strýcová, and the third round of Wimbledon against Angelique Kerber.
As a wildcard in the tournament of New Haven, she made it into the quarterfinal after an epic against Andrea Petkovic (4–6, 7–6 (4), 7–6 (6)) but was eventually beaten by Samantha Stosur 3–6, 6–4, 3–6.
In the US Open, she lost in the first round to Italian Sara Errani.
Flipkens finished the season as no. 46 in the world.
At the end of the season, she took part in the first edition of the International Premier Tennis League, where she played for the Manila Mavericks and was teammates with – amongst others – Maria Sharapova, Andy Murray and Jo-Wilfried Tsonga. During this two-and-a-half week during event, Flipkens mainly excelled as a mixed doubles player, alongside multiple champion Daniel Nestor. The Manila Mavericks ended third in the competition.
Flipkens started 2015 with a knee injury and only won one match during the Australian season (against Johanna Larsson in Auckland). In the Australian Open 2015, she was beaten by friend and doubles partner Dominika Cibulková 3–6, 6–3, 6–1. During the Fed Cup, she and her teammates failed to bring Belgium back to the World Group II after the team lost their final tie against Croatia.
She reached her first quarterfinal of the season in Katowice, where she lost to compatriot Alison Van Uytvanck. During the tournament of Stuttgart in April, she was forced to retire because of an 11.5 cm tear in her upper leg. This healed better than expected and against all the odds she made it into the French Open, where she lost the first round against Elena Vesnina.
In Wimbledon, she played the second round against former no. 1 Victoria Azarenka, but lost 6–4, 6–2. After Wimbledon, she fell out of the top 100 for the first time since 2012.
In July, she played the semifinal of Istanbul (beating – amongst others – Francesca Schiavone and Alizé Cornet) and the quarterfinal of Baku. Thanks to these two good results, she made it back into the top 100. She proceeded to play the final of 100k ITF Vancouver, where she lost to Johanna Konta from Britain.
At the US Open, she was beaten in the first round by Varvara Lepchenko. In doubles, she played alongside Laura Robson. They reached the second round, where they were beaten by fifth seeds Caroline Garcia and Katarina Srebotnik.
After the US Open, Flipkens was diagnosed with a cyst on the wrist, which made her unable to play, resulting in her dropping out of the top 100 again. She made her comeback in the Linz Open. This comeback was successful; Flipkens reached the semifinal (beating – amongst others – former number 1 Caroline Wozniacki) before eventually falling to Anastasia Pavlyuchenkova 6–3, 3–6, 6–2.
She officially finished the year 2015 as no. 93 in the world.
At the end of the season, Flipkens continued to play a couple of WTA 125k's, in Poitiers, Hua Hin and Taipei. Poitiers and Hua Hin were no success, as she respectively lost in the second and in the first round. In Taipei, however, Flipkens managed to reach the semifinal. This caused her ranking to rise up to 85 after the official season's end rankings.
Flipkens started the year with a quarterfinal in Auckland. She then reached the second round of the Australian Open, where she lost to 3rd seed Garbiñe Muguruza (6–4, 6–2). In doubles, she and her partner Dominika Cibulkova had their best Grand Slam result yet. They reached the 4th round where they lost to Anastasia and Arina Rodionova (5–7, 6–2, 6–4).
In the tournaments of St-Petersburg and Doha, Flipkens lost in the first round. In the following tournament in Monterrey, she reached the final after beating Francesca Schiavone (6–3, 7–6), Alison Van Uytvanck (6–2, 4–6, 6–3), Johanna Konta (6–3, 6–7, 6–1) and Anett Kontaveit (7–6, 6–4). In the final, she eventually lost to Heather Watson (3–6, 6–2, 6–3). This good result was rewarded with a place back in the top 60, at no. 59.
After the tournaments of Indian Wells and Miami (where she respectively lost in the final qualifying round against Aliaksandra Sasnovich and the second round against Madison Keys), Flipkens went on to play the quarterfinals of Katowice, where she was defeated by Camila Giorgi (6–2, 5–7, 6–4).
Flipkens was part of the Belgian Fed Cup team against Serbia as the two nations were competing for a spot in World Group II. As Belgium's second player (after Yanina Wickmayer), Flipkens played two singles matches. She lost the first one against Aleksandra Krunic but beat the 18-year-old Ivana Jorovic in the decider, and with this victory ensured Belgium of a place back into World Group II after three consecutive years in the Europe-Africa Zone I.
The clay season didn't go well for Flipkens. She was plagued by a wrist injury, and only managed to win one match (against Donna Vekic in Istanbul) in the clay tournaments she entered. In the French Open, she was destroyed by Alizé Cornet in the first round (6–1, 6–0). In doubles, she and her partner Dominika Cibulkova reached the second round, where they retired vs. 4th seeds Babos/Shvedova.
In the Mallorca Open, Flipkens stunted versus freshly crowned French Open victor and world's number 2, Garbine Muguruza, beating her in the first round with 6–3, 6–4. She proceeded to reach the semifinal, where she was eventually beaten by the future tournament winner, Caroline Garcia, with 6–4, 4–6, 6–1. Flipkens also reached the semifinal in doubles, together with her partner Ana Ivanovic.
In Wimbledon, Flipkens reached the second round, where she lost to 9th seed Madison Keys with 6–4, 4–6, 6–3.
Flipkens entered her first Olympics ever in both singles and doubles. In singles, she stunned the gold medalist from Sydney 2000, and three times doubles champion, Venus Williams in the first round, defeating her after an epic match with 4–6, 6–3, 7–6(5). In the second round, Flipkens beat Lucie Šafářová, who retired after losing the first set with 6–2. Eventually, Flipkens was beaten in R16 by Laura Siegemund from Germany, with 6–4, 6–3. In doubles, Flipkens played alongside Yanina Wickmayer. In the first round, the Belgians faced Kazakh duo Shvedova/Voskoboeva, who retired after losing the first set with 6–1. However, Flipkens and Wickmayer were defeated in R16 by the Spanish team Muguruza/Suarez Navarro, the 4th seeds, with 7–5, 2–6, 6–2.
In the US Open, Flipkens didn't get past the first round as she was demolished by 5th seed Simona Halep with 6–0, 6–2. In doubles, she also lost in the 1st round, alongside Belinda Bencic.
In Seoul, Flipkens won her first WTA doubles title, partnering Johanna Larsson from Sweden. They defeated Akiko Omae and Peangtarn Plipuech in the final with 6–2, 6–3.
At the end of the season, Flipkens took part in the IPTL for the third time in a row, as a member of the Micromax Indian Aces. The team ended up as runner-up, losing to the Singapore Slammers with 30–14. She was one of the players to receive the Fed Cup Commitment Award at the end of 2016 for being the Belgian player who's represented her country in the Fed Cup the longest: a total of 13 years in 2016. Flipkens was also nominated for a WTA Award in the category of Shot of the Year for a spectacular behind-the-back winner she scored against Kristyna Pliskova in Seoul. She was voted into the final but the award would eventually go to Agnieszka Radwanska.
Flipkens finished the year as no. 63 in the world.
Flipkens began the 2017 year at the 2017 ASB Classic. She lost in the 1st round to 8th seed and eventual finalist Ana Konjuh 6-4, 3-6, 6-3. Next, Flipkens competed at the 2017 Hobart International. In the 1st round, she beat wildcard Jaimee Fourlis 7-6(10), 6-4. In the 2nd round, Flipkens was defeated by 3rd seed and eventual finalist Monica Niculescu 6-3, 6-2. At the 2017 Australian Open, Flipkens lost in the 1st round to 9th seed Johanna Konta 7-5, 6-2.
After the Australian Open, Flipkens played qualifying at the 2017 St. Petersburg Ladies' Trophy. Flipkens made it to the main draw after beating Viktoriya Tomova, Paula Cristina Gonçalves, and 7th seed Donna Vekić. In the 1st round, she lost to Alizé Cornet 6-4, 6-2. In the Fed Cup tie against Romania, Flipkens won her singles match against Monica Niculescu and thusly aided the Belgian team in securing a place in the World Group play-offs, since the team beat the Romanians with 3–1. At the 2017 Hungarian Ladies Open, Flipkens was defeated in the 1st round by qualifier Aliaksandra Sasnovich 4-6, 6-4, 6-1.
Flipkens reached her first quarterfinal of the season in the WTA-tournament of Acapulco, where she lost to Kristina Mladenovic. In the prestigious tournament of Indian Wells, she beat 17-year-old talent CiCi Bellis but got beaten by Garbine Muguruza in the second round. In Miami she was beaten by Dominika Cibulkova in the third round.
Alongside Johanna Larsson, Flipkens reached another doubles final in Nürnberg. The pair was beaten by Nicole Melichar and Anna Smith with 3–6, 6–3, 11–9.
At the French Open, Flipkens reached the 2nd round but lost to Samantha Stosur. In doubles, she played together with ex-winner Francesca Schiavone. They made it to the quarterfinals.
Flipkens describes herself as "an all court player" whose biggest strength is her "serve and all round game". She makes up for her short height and relative lack of physical strength with her good forehand and serve, her quickness and agility, and her ability to play almost every shot (which results in her frequently being awarded with "Shot of the Day" by the WTA). Her trademark shot is backhand slice and she often plays serve-and-volley. She prefers fast courts. Her favorite surface is grass.
Flipkens is sponsored by Babolat for tennis rackets. Her glasses are sponsored by Oakley. She used to wear Adidas clothing, but as of 2017 she launched her own clothing line and now plays in clothes she's designed herself. She also designed the official outfits of the Belgian Fed Cup team.