In seventh grade, she made the decision to homeschool, giving her more time on the practice courts and an opportunity to play more tournaments.

[4] While the decision proved to be very beneficial for her career, Oudin admits envying her twin sister's experiences at a regular school.

[8] In April 2008, she received a wildcard at the WTA tournament in Miami where she lost in the first round to Tathiana Garbin, in three sets.

[10] During the Fed Cup tie versus France, Oudin won both of her rubbers over Pauline Parmentier and Julie Coin.

[12] Seeded second at the Cellular South Cup, Oudin made it to the quarterfinal round where she lost to qualifier and eventual finalist Sofia Arvidsson.

[16] In January, she obtained an invitation to play at the Hong Kong Tennis Classic with compatriots Venus Williams and John McEnroe.

[citation needed] Ranked 82 at the Monterrey Open, Oudin won her first-round match over fellow American Vania King 6–4, 6–1.

[29] Moving on to Miami, Oudin started the tournament well with a first-round win over Julia Görges[30] but was defeated in the second by 29th seed Daniela Hantuchová, 6–1, 6–3.

[32] In the 2011 Fed Cup World Group play-offs tie versus Germany, Oudin lost both of her rubbers to Julia Görges and Andrea Petkovic.

[39] Competing at the Internationaux de Strasbourg, she lost in the first round to seventh seed Anabel Medina Garrigues in straight sets.

[40] Ranked 88 at the French Open, Oudin lost in the first round to fifth seed and defending champion Francesca Schiavone, 2–6, 0–6.

[48] However, in mixed doubles, she and Jack Sock captured the title defeating the eighth seeded Argentine pairing of Gisela Dulko and Eduardo Schwank in the final.

[50] Seeded seventh at the ITF Albuquerque, Oudin lost in the second round to eventual champion Regina Kulikova.

Qualifying for the Charleston Cup, Oudin lost in the first round to tenth seed Anabel Medina Garrigues.

[54] At the Dothan Pro Tennis Classic, Oudin was defeated in the second round by fourth seed Mirjana Lučić.

On April 29, Oudin won the $50k Clay Court Classic defeating second seed and fellow American Irina Falconi in the final.

In the main draw, Oudin advanced to her first WTA Tour final defeating tenth seed Sorana Cîrstea, qualifier Michelle Larcher De Brito, Elena Vesnina, Irina Falconi, and eighth seed Ekaterina Makarova.

107 ranked Oudin was unseeded and lost to 15th seed Lucie Šafářová of the Czech Republic in straight sets.

Oudin started her 2013 season at the Sydney International, and lost in the second round of qualifying to Estrella Cabeza Candela.

Seeded eighth at The Oaks Club Challenger, Oudin was defeated in the first round by Estrella Cabeza Candela.

She began her preparation for the French Open at the Family Circle Cup where she lost in the first round to ninth seed, 2007 champion, and eventual finalist Jelena Janković.

[72] Getting past qualifying at the Italian Open, Oudin won her first-round match when her opponent, Ekaterina Makarova, retired due to a left achilles tendon injury.

[75] At the French Open, Oudin upset 28th seed Tamira Paszek in the first round[76] but lost in the second to Jie Zheng.

[82] Seeded sixth at the Coleman Vision Championships, Oudin lost in her second-round match to Petra Rampre.

Oudin won the Party Rock Open, a $50k tournament in Las Vegas, beating compatriot CoCo Vandeweghe in the final.

Oudin competed in her final tournament of the season at the South Seas Island Resort Pro Classic and lost in the first round to compatriot Allie Kiick.

[85] In November 2009, Oudin lost both of her matches (against Flavia Pennetta and Francesca Schiavone) in the championship round of the 2009 Fed Cup.

[86] In the 2010 Fed Cup, Oudin led the US to a 4–1 victory over France by defeating Pauline Parmentier and Julie Coin.

Contrary to expectations, lower ranked CoCo Vandeweghe was chosen over Oudin for the first singles match against Francesca Schiavone.

In the 2011 Fed Cup World Group tie against Belgium, Oudin lost both her singles matches against Kim Clijsters and Yanina Wickmayer.