In 2019, Medvedev won the inaugural Diriyah Tennis Cup. At the time, Medvedev defeated David Goffin, Jan-Lennard Struff, and Fabio Fognini to win the Diriyah Tennis Cup.
Due to the pandemic, the Diriyah Tennis Cup was postponed in 2020 and 2021. In December, the Diriyah Tennis Cup will have its second competition. Along with Medvedev, other players competing include Alexander Zverev, Nick Kyrgios, Stefanos Tsitsipas, Taylor Fritz, and Andrey Rublev. Medvedev said when asked why he would prevail in the competition. "I want to do it again because I played extremely well there the first time"
The Diriyah Tennis Cup was Medvedev's first major victory. The Russian is now the world's top player and a Grand Slam champion. This year's Diriyah Tennis Cup is anticipated to include some of the top athletes in the game. As a result, Medvedev is urging Saudis to attend a top-notch tennis tournament in Riyadh.