Djokovic is aiming to become only the third man in the Open era to win 100 Tour-level titles, having reached 99 by completing a career ‘Golden Slam’ at the Paris 2024 Olympics.
Jimmy Connors and Roger Federer are the only players to have reached the landmark.
But, after being stunned by Czech teenager Jakub Mensik in the Miami Open final in his previous attempt at reaching the landmark, that wait goes on for Djokovic.
Making his 18th appearance in Monte Carlo, the 2013 and 2015 champion made the perfect start by breaking Tabilo’s serve in the opening game.
But world number 32 Tabilo once again had the measure of the former world number one, against whom he has now achieved the two biggest wins of his career.
The 27-year-old produced an excellent response following his early setback, twice breaking an out-of-sorts Djokovic to turn the first set around.
Tabilo then struck what proved the decisive blow in the third game of set two, with Djokovic conceding on a second break point after inviting pressure with costly errors.
The Serb attempted to hang on, but Tabilo saved two break points to move within one game of victory before sealing it on his second match point.
He will face Bulgarian 15th seed Grigor Dimitrov or wildcard Valentin Vacherot next.
