World Tennis Championship

Novak Djokovic started the season by playing the World Tennis Championship, an exhibition tournament on the last week of 2018. He defeated Karen Khachanov and Kevin Anderson to win the tournament for a fourth time.

Qatar Open

Djokovic's first official tournament was the Qatar Open. He reached the semifinals by defeating Damir Džumhur, Márton Fucsovics and Nikoloz Basilashvili, but lost in three sets to eventual champion Roberto Bautista Agut.^[1]

Australian Open

Djokovic entered the Australian Open as the top seed. He defeated qualifier Mitchell Krueger, 2008 finalist Jo-Wilfried Tsonga, 25th seed Denis Shapovalov, 15th seed Daniil Medvedev, 8th seed Kei Nishikori, and 28th seed Lucas Pouille to reach the final, in which he beat 2nd seed Rafael Nadal in straight sets to win his 15th Major and a record 7th Australian Open.^[2]

Indian Wells Masters

Djokovic's next tournament was the Indian Wells Masters, where he received a first round bye along with 31 seeded players. He won his first match since Australian Open title against Bjorn Fratangelo, but was defeated in two sets by Philipp Kohlschreiber in the third round.^[3]

Miami Open

After his early exit at Indian Wells, Djokovic played at the Miami Open where he had previously won six times. After defeating Bernard Tomic and Federico Delbonis, Djokovic faced Roberto Bautista Agut. Djokovic won the first set and went a break up in second set, before a rain delay that seemingly disrupted his momentum. Djokovic eventually lost the match in three sets. After 41 straight wins, it was the first time Djokovic had lost in Miami after winning the first set. After the match, Djokovic admitted being affected by off-court distractions during the tournament.^[4]

Monte-Carlo Masters

Djokovic's clay court season commenced at the Monte Carlo Masters, which was played in the third week of April.^[5] Djokovic received an opening round bye, and made his clay court debut against Philipp Kohlschreiber in the second round, which he won in three tight sets. He reached the quarterfinals, where he lost to Daniil Medvedev in three sets.^[6]

Madrid Open

Djokovic followed his Monte Carlo quarterfinal run with a record-tying 33rd Masters 1000 title at the Madrid Open, defeating Stefanos Tsitsipas in the finals. Djokovic won the tournament without dropping a set, securing his third career title at the event.

Italian Open

At the 2019 Italian Open, Djokovic defeated Denis Shapovalov and Philipp Kohlschreiber in straight sets to progress to the quarterfinals. In his next match, Djokovic had to fend off two match points to prevail over Juan Martin del Potro in three sets. In the semifinals, Djokovic defeated Diego Schwartzman in three sets to progress to the finals, where he faced his rival Rafael Nadal for the first time since the 2019 Australian Open. Their 54th encounter saw Nadal prevailing over Djokovic in three sets, that included a bagel in the first set.

French Open

Djokovic entered the French Open aiming to win a fourth straight grand slam title, and becoming the first man in Open Era to win all four grand slams at least twice. He breezed through the tournament and reached the semifinals without dropping a set, after defeating Alexander Zverev in the quarterfinals. In the semifinals, he narrowly lost to Dominic Thiem in a close five set match which lasted two days due to numerous rain delays, ending his 26-match winning streak in grand slam tournaments.

Wimbledon

At Wimbledon, he won his sixteenth Grand Slam, defending his title to win the tournament for a fifth time by defeating Roger Federer in an epic five set final that lasted four hours and fifty seven minutes, the longest in Wimbledon history. Djokovic saved two championship points in the fifth set en route to winning the title and the match also marked the first time a fifth set tiebreak was played in the men's singles of Wimbledon at 12 games all.^[7][8]

Cincinnati Masters

Djokovic played his US open warm up in Cincinnati. He got a bye to the second round and then beat American Sam Querrey, Spain's Pablo Carreno Busta and France's Lucas Pouille, all in straight sets. In the semifinals however, he was defeated by Russia's Daniil Medvedev in 3 sets after Djokovic was up a set. Medvedev went on to win the title.

US Open

At the US Open, Djokovic was unable to defend his title, falling to Stan Wawrinka in the fourth round, while down two sets and a break before retiring due to injury. The defeat prevented Djokovic from sweeping three of the four Grand Slams that year, a feat that he achieved in 2011 and 2015.

Japan Open

Novak Djokovic won his first Japan Open title and the 76th of his career with a 6–3 6–2 win over Australian John Millman in the final in Tokyo on Oct 06. 2019. It was a triumphant return for Djokovic after his shoulder injury causing him to withdraw from the U.S. Open in the fourth round.^[9]

Shanghai Masters

Djokovic entered Shanghai Masters as top seed and defending champion but could not defend his title. He defeated Denis Shapovalov in second round and John Isner in third round in straight sets to enter quarter-finals. He lost in quarter-finals to Stefanos Tsitsipas in three sets 6–3, 5–7, 3–6.^[10]

Paris Masters

Djokovic started his campaign with a tough victory over Frenchman Corentin Moutet. From then on, he beat Brit Kyle Edmund, Stefanos Tsitsipas (for the loss of only three games), Grigor Dimitrov and Denis Shapovalov in the final. He did not lose a set in the tournament and clinched a record-extending fifth title in Paris-Bercy.

ATP Finals

Djokovic was placed in the Bjorn Borg group, along with Roger Federer, Dominic Thiem and Matteo Berrettini. He started off with a convincing straight sets win over Berrettini, but lost narrowly to Thiem in a third set tiebreak and to Federer in straight sets, losing the opportunity to finish as the year-end number 1.

Davis Cup Finals

Djokovic helped Serbia to win their group with victories over Yoshihito Nishioka and Benoit Paire, as the country went 5–1 in their matches. In the quarterfinals against Russia, Djokovic won the second rubber against Karen Khachanov but could not avoid the defeat, as he and Viktor Troicki lost a pivotal doubles match to the Russian pair of Khachanov and Rublev.

Singles: 6 (5 titles, 1 runner-up)

Result	W–L	Date	Tournament	Tier	Surface	Opponent	Score
Win	1–0	Jan 2019	Australian Open, Australia (7)	Grand Slam	Hard	Rafael Nadal	6–3, 6–2, 6–3
Win	2–0	May 2019	Madrid Open, Spain (3)	Masters 1000	Clay	Stefanos Tsitsipas	6–3, 6–4
Loss	2–1	May 2019	Italian Open, Italy	Masters 1000	Clay	Rafael Nadal	0–6, 6–4, 1–6
Win	3–1	Jul 2019	Wimbledon, United Kingdom (5)	Grand Slam	Grass	Roger Federer	7–6(7–5), 1–6, 7–6(7–4), 4–6, 13–12(7–3)
Win	4–1	Oct 2019	Japan Open, Japan	500 Series	Hard	John Millman	6–3, 6–2
Win	5–1	Nov 2019	Paris Masters, France (5)	Masters 1000	Hard (i)	Denis Shapovalov	6–3, 6–4