Roger Federer defeated Novak Djokovic in the final, 6–1, 7–5 to win the men's singles tennis title at the 2009 Cincinnati Masters.
Novak Djokovic defeated Gaël Monfils in the final, 6–2, 5–7, 7–6(7–3) to win the singles tennis title at the 2009 Paris Masters. It was his first Paris Masters title, and the first of an eventual record six titles at the event.
Robin Söderling defeated Gaël Monfils in the final, 6–1, 7–6(7–1) to win the singles tennis title at the 2010 Paris Masters.
Roger Federer defeated Tomáš Berdych in the final, 3–6, 7–5, 7–5 to win the men's singles tennis title at the 2012 Madrid Open. With the win, Federer won his record-tying 20th Masters title and third title at Madrid.
Defending champion Roger Federer defeated Novak Djokovic in the final, 7–6(7–1), 6–3 to win the men's singles tennis title at the 2015 Cincinnati Masters. He won the title without losing a set or having his serve broken for the second time, after 2012. It marked the first time Federer defeated the world No. 1 and No. 2 players in consecutive matches en route to a title. It was Djokovic's fifth runner-up finish without winning the title; he would eventually do so in 2018.
Rafael Nadal defeated Gaël Monfils in the final, 7–5, 5–7, 6–0 to win the singles tennis title at the 2016 Monte-Carlo Masters. It was his record-extending ninth Monte-Carlo Masters title.
Novak Djokovic defeated Borna Ćorić in the final, 6–3, 6–4 to win the singles tennis title at the 2018 Shanghai Masters. It was his record fourth Shanghai Masters title, and 32nd Masters 1000 title overall. He did not lose a single set and did not have his serve broken throughout the entire tournament.
Novak Djokovic defeated Rafael Nadal in the final, 6–3, 6–2, 6–3 to win the men's singles tennis title at the 2019 Australian Open. It was his record-breaking seventh Australian Open title and 15th major title overall, surpassing Pete Sampras for third place on the all-time list. Djokovic and Nadal were also in contention for the world No. 1 singles ranking; Djokovic retained the top ranking by reaching the fourth round. Nadal attempted to become the first man in the Open Era to achieve a double career Grand Slam.
Dominic Thiem defeated Roger Federer in the final, 3–6, 6–3, 7–5 to win the men's singles tennis title at the 2019 Indian Wells Masters. It was his maiden ATP Tour Masters 1000 title, and he became the first Austrian to win a Masters title since Thomas Muster won the 1997 Miami Open.
Roger Federer defeated the defending champion John Isner in the final, 6–1, 6–4 to win the men's singles tennis title at the 2019 Miami Open. It was Federer's fourth Miami Open title, his 28th and final Masters singles title, and his 101st career singles title overall.
Novak Djokovic defeated Stefanos Tsitsipas in the final, 6–3, 6–4 to win the men's singles tennis title at the 2019 Madrid Open. With the win, Djokovic tied Rafael Nadal's record of 33 Masters 1000 singles titles. He did not lose a single set in the entire tournament.
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.
Rafael Nadal defeated Daniil Medvedev in the final, 7–5, 6–3, 5–7, 4–6, 6–4 to win the men's singles tennis title at the 2019 US Open. It was his fourth US Open title and 19th major title overall. Nadal's victory meant that every major title since the beginning of 2017 had been won by either himself (5), Novak Djokovic (4) or Roger Federer (3). This was the first time since 2006–08 that Djokovic, Federer, and Nadal had claimed all four major singles titles in three consecutive years.
Daniil Medvedev defeated Alexander Zverev in the final, 6–4, 6–1 to win the singles tennis title at the 2019 Shanghai Masters. He did not drop a set en route to the title.
Novak Djokovic defeated Denis Shapovalov in the final, 6–3, 6–4 to win the singles tennis title at the 2019 Paris Masters. It was his record-extending fifth Paris Masters title, and he did not drop a set en route.
Two-time defending champion Novak Djokovic defeated Daniil Medvedev in the final, 7–5, 6–2, 6–2 to win the men's singles tennis title at the 2021 Australian Open. It was his record-extending ninth Australian Open title and his 18th major title overall. With his fourth round win against Milos Raonic, Djokovic joined Roger Federer as only the second man with 300 or more match wins in major singles competitions.
Novak Djokovic defeated Stefanos Tsitsipas in the final, 6–7(6–8), 2–6, 6–3, 6–2, 6–4 to win the men's singles tennis title at the 2021 French Open. It was his second French Open title and 19th major title overall. With the win, he became the first man to achieve the double Career Grand Slam in the Open Era, and the first player in the Open Era to win a major after coming back from two sets to love down in two matches during the same major. Tsitsipas became the first Greek player to reach a major final. It also marked the second consecutive year a man trailed by two sets in a major final yet rallied to win, following Dominic Thiem's victory at the 2020 US Open.
Alexander Zverev defeated Matteo Berrettini in the final, 6–7(8–10), 6–4, 6–3 to win the men's singles tennis title at the 2021 Madrid Open. It was Zverev's fourth Masters 1000 title, his first since Madrid 2018, and his 15th career ATP Tour singles title overall. Berrettini was in contention to become the second Italian to be a Masters 1000 champion.
Rafael Nadal defeated the defending champion Novak Djokovic in the final, 7–5, 1–6, 6–3 to win the men's singles tennis title at the 2021 Italian Open. It was his record-extending 10th Italian Open title and record-equaling 36th Masters 1000 title overall. Nadal saved two match points en route to the title, in his third round match against Denis Shapovalov. This was also the fourth time that Nadal had won a tournament on 10 or more occasions, making him the only tennis player with the feat.
Two-time defending champion Novak Djokovic defeated Matteo Berrettini in the final, 6–7(4–7), 6–4, 6–4, 6–3 to win the gentlemen's singles tennis title at the 2021 Wimbledon Championships. It was his sixth Wimbledon title and 20th major title overall, tying Roger Federer and Rafael Nadal's all-time record total of men's singles titles.
Novak Djokovic 
Stefanos Tsitsipas 
