Novak Djokovic is preparing for the Madrid Masters in Marbella. The 24-time Major winner trained at his favorite Spanish resort with Lloyd Harris, shaping up his game ahead of the fourth Masters 1000 event of the season.

Novak is 12-6 in 2025, reaching one final and still seeking that elusive 100th ATP title. The Serb will try to lift his fourth trophy at Caja Magica, conquering the event in the Spanish capital in 2011, 2016 and 2019.

Djokovic ended his most recent Madrid Masters campaign in the semi-final three years ago, falling to Carlos Alcaraz after an incredible battle that went down to the wire.

The Serb started the current season in Brisbane and lost to Reilly Opelka. He defeated Alcaraz in the Australian Open quarter-final but injured his right thigh. He gave everything to recover for the semi-final, only to retire against Alexander Zverev after the opening set.

Djokovic returned to action in Doha and fell to Matteo Berrettini in the first round. The legend traveled to the USA and experienced another early loss in Indian Wells, this time to a lucky loser Botic van de Zandschulp.

The veteran competed in Miami for the first time since 2019 and found his A-game. Novak chased his 100th ATP title against the young gun Jakub Mensik and finished in the runner-up spot following a tight 7-6, 7-6 defeat.

Novak could not repeat that run in Monte Carlo after losing to Alejandro Tabilo 6-3, 6-4 in an hour and 27 minutes. Dealing with a viral infection since Miami, Djokovic entered Monte Carlo with low expectations. However, he played way below his best and surprised even himself.

Tabilo secured his second win from as many duels against the 24-time Major champion. Novak struggled on serve and return, taking 17 points fewer than Alejandro. The Chilean faced only three break points and saved two to keep the pressure on the other side.

Djokovic served at 54% and gave away 45% of the points in his games, playing against eight break points and experiencing three breaks. Tabilo landed 16 winners and unforced errors. He welcomed almost 30 mistakes from the 24-time Major winner, mostly from his forehand.

Novak trailed in the shortest exchanges up to four shots after missing service winners, losing the match in that area. The 37-year-old clinched a break in the first game of the duel with a volley winner. He missed a backhand in the next one and brought his rival back to the positive side.

Alejandro served well in games three and five and fired a backhand crosscourt winner at 3-2 to provide a break and forge the advantage. The Chilean closed the seventh game with a service winner and landed more direct points two games later for 6-3 in 37 minutes.

Novak saved a break point at 1-1 in the second set with an ace before Alejandro seized the second with a deep return. Doing everything right, Tabilo cracked winners in the fourth game to cement the lead and open a 3-1 gap.

The Chilean held at love in game six for 4-2 before the Serb generated break chances in game eight. However, Novak squandered them, especially the second, allowing his rival to close the game with a winner at the net and move 5-3 in front.

Djokovic saved a match point on serve in the ninth game with a drop shot winner and landed a smash to close the game and extend the battle. Alejandro served for the win at 5-4 and moved over the top with a service winner, earning his second win from as many duels against the legend.