the WTA rankings for the first time since May 2015. As the top seed at the Internazionali Femminili di Brescia, Kanepi won the tournament beating sixth seed Martina Trevisan in the final. Kanepi kicked off her grass-court season at the Ilkley Trophy. Despite being the top seed, she lost in her quarterfinal match to seventh seed Ekaterina Alexandrova. At the Eastbourne International, Kanepi was defeated in the second round by fifth seed Jeļena Ostapenko. At the Wimbledon Championships, she lost in the first round to qualifier Sara Sorribes Tormo. Seeded eighth at the first edition of the Moscow River Cup, Kanepi was defeated in the second round by lucky loser and eventual champion, Olga Danilović. Coming through qualifying at the Western & Southern Open, Kanepi reached the second round where she lost to 16th seed Ashleigh Barty. At the US Open, Kanepi upset top seed Simona Halep in the first round becoming the first player in US Open history and just sixth in Grand Slam history to beat the top-seeded player in the first round. She then defeated qualifier Jil Teichmann and Rebecca Peterson to advance to the fourth round and was defeated by 17th seed Serena Williams. Kanepi didn't play any more tournaments for the rest of the season. She ended the year ranked 58. 2019 Kanepi played her first tournament of 2019 at the Australian Open. After taking the first set in a tiebreak, Kanepi was defeated in the first round by top seed Simona Halep. Seeded seventh at the Indian Wells Challenger, Kanepi lost in the third round to 11th seed Zarina Diyas. At the Indian Wells Open, Kanepi was defeated in the second round by 15th seed Julia Görges. Entering the Miami Open draw as a qualifier, Kanepi lost in the first round to Alison Riske. Kanepi began her clay-court season at the Charleston Open. She reached the third round beating Veronika Kudermetova and sixth seed Elise Mertens. She was defeated in her third-round match by eleventh seed Danielle Collins. At the Madrid Open, Kanepi lost in the final round of qualifying to Kristýna Plíšková. Ranked 88 at the French Open, Kanepi advanced to the fourth round for the first time since 2008 after wins over 18th seed Julia Görges, Zhang Shuai, and Veronika Kudermetova. She was defeated in her fourth-round match by 31st seed Petra Martić. At the Wimbledon Championships, Kanepi lost in the second