the first set 6–3 against world No. 2 pairing Chan Hao-ching/Chan Yung-jan, they lost in three sets. At the Indian Wells Open, Vesnina fell in the first round of the qualifying to American wildcard Julia Boserup. In doubles, Vesnina once again partnered Daria Kasatkina but lost in the second round, to eventual finalists Julia Görges/Karolína Plíšková. In the Miami Open, Vesnina managed to get past qualifying after beating Kateryna Kozlova, avenging her loss in St. Petersburg, and Tsvetana Pironkova. She was drawn to face fellow qualifier Jana Čepelová in the first round and won in straight sets. In the second round, Vesnina caused a huge upset when she beat former world No. 1 and seven-time Grand Slam champion Venus Williams in three sets. Vesnina then faced Britain Johanna Konta but lost. In doubles, Vesnina and Kasatkina fell to two-time Grand Slam champion Bethanie Mattek-Sands/Lucie Šafářová in the second round. At the Charleston Open, the 85th-ranked Vesnina became the first qualifier to ever reach the championship match in the tournament's 44-year history, where she faced a determined Sloane Stephens. Stephens ended up prevailing 7–6, 6–2 as the fatigue of 718 minutes – nearly 12 hours – of tournament tennis appeared to take a toll on Vesnina in the second set. Vesnina again subdued the qualification, now in Madrid. In the second round she fell to Kvitová. In doubles, she and Makarova played their first tournament together since late 2015 and reached the semifinals. In Rome, Vesnina could not qualify for the main draw. However, with Makarova she reached the final, losing to Hingis/Mirza. At Wimbledon, Vesnina competed in her first Grand Slam semifinal with victories over Tamira Paszek, Andrea Petkovic, and Julia Boserup in the first three rounds before outlasting doubles partner Makarova in three sets to advance to her first Grand Slam quarterfinal. She then defeated Dominika Cibulková to continue her resurgence into the semifinals, where she was handily defeated by world No. 1 and eventual champion, Serena Williams, in 48 minutes, the quickest Wimbledon semifinal in the history of the championships. Vesnina and Makarova finally won their first tournament title of 2016 at the Rogers Cup and then won the gold medals at the Summer Olympics for Russia. In singles, Vesnina lost to tenth seed Madison Keys in the Rogers Cup and to Elina Svitolina in Connecticut. Seeded 19th in the US Open, Vesnina defeated Anett Kontaveit and Annika