Alexandr Dolgopolov was the defending champion, but withdrew before the tournament began.
Defending champion Rafael Nadal defeated Novak Djokovic in the final, 6–0, 4–6, 6–1 to win the men's singles tennis title at the 2019 Italian Open. It was his record-extending ninth Italian Open title and record 34th ATP Masters 1000 title.
Fabio Fognini was the defending champion, but he chose to compete in Umag instead.
Juan Ignacio Londero was the defending champion, but lost to Laslo Đere in the quarterfinals.
The 2020 Chile Open was a men's tennis tournament played on outdoor clay courts. It was the 22nd edition of the Chile Open, and part of the ATP 250 of the 2020 ATP Tour. It took place in Santiago, Chile from 24 February through 1 March 2020. Unseeded Thiago Seyboth Wild, who entered on a wildcard, won the singles title.
This was the first edition of the tournament, primarily organised due to the cancellation of many tournaments in 2020, due to the COVID-19 pandemic.
Diego Schwartzman defeated Francisco Cerúndolo in the final, 6–1, 6–2 to win the men's singles tennis title at the 2021 Argentina Open.
Alexander Zverev defeated top seed Stefanos Tsitsipas in the final, 6–4, 7–6(7–3) to win the men's singles tennis title at the 2021 Mexican Open.
Pablo Carreño Busta defeated Jaume Munar in the final, 6–1, 2–6, 6–4 to win the inaugural Men's Singles tennis title at the 2021 Andalucía Open. Notably, this was the first tournament in ATP history to feature 4 semifinalists from the same nation.
Stefanos Tsitsipas defeated Andrey Rublev in the final, 6–3, 6–3 to win the singles tennis title at the 2021 Monte-Carlo Masters. It was his first ATP Tour Masters 1000 title, making him the first Greek to win a Masters tournament. Rublev was also in contention for his maiden Masters 1000 title.
Andrey Rublev was the defending champion, but chose to not defend his title as he and other Russian Olympic athletes were sent to Yuzhno-Sakhalinsk for training sessions.
Carlos Alcaraz defeated Richard Gasquet in the final, 6–2, 6–2 to win the singles tennis title at the 2021 Croatia Open. It was his first ATP Tour title. With the victory, Alcaraz became the youngest player to win an ATP Tour title since Kei Nishikori at the 2008 Delray Beach International Tennis Championships.
Miomir Kecmanović was the defending champion, but chose to compete at the Summer Olympics instead.
Cameron Norrie defeated Nikoloz Basilashvili in the final, 3–6, 6–4, 6–1 to win the men's singles tennis title at the 2021 Indian Wells Masters. It was his first ATP Tour Masters 1000 title, and he became the first Briton to win the title. Basilashvili became the first Georgian to reach a Masters-level final since Alex Metreveli in 1968, and the first to do so while representing Georgia as an independent nation.
Casper Ruud defeated the defending champion Diego Schwartzman in the final, 5–7, 6–2, 6–3 to win the singles title at the 2022 Argentina Open.
The 2022 Chile Open was a men's tennis tournament played on outdoor clay courts. It was the 24th edition of the Chile Open, and part of the ATP 250 of the 2022 ATP Tour. It took place in Santiago, Chile from 21 through 27 February 2022.
Francisco Cerúndolo defeated Sebastián Báez in the final, 7–6(7–4), 6–2 to win the men's singles tennis title at the 2022 Swedish Open. It was his maiden ATP Tour title.
Defending champion Casper Ruud defeated Matteo Berrettini in the final, 4–6, 7–6(7–4), 6–2 to win the singles tennis title at the 2022 Swiss Open Gstaad.
Carlos Alcaraz defeated Cameron Norrie in the final, 6–3, 7–5 to win the singles tennis title at the 2023 Argentina Open.
Alexander Zverev defeated Laslo Djere in the final, 7–5, 6–3 to win the men's singles tennis title at the 2023 Hamburg European Open.
Thiago Seyboth Wild 
Casper Ruud 
