Qualifying for the main draw, an 18-year-old Novak Djokovic made the Monte Carlo debut against Roger Federer in 2006. It was the first clash in their extraordinary rivalry, and Federer scored a 6-3, 2-6, 6-3 triumph in an hour and 49 minutes.
After gaining over 100 positions on the ATP list in 2005, the young Serb wanted in the following season, carving his way towards the top-20 and showing incredible skills against world no. 2 in the Principality, especially in the second set when he had the upper hand on the court.
They had a similar number of unforced errors, and Novak pushed Federer's backhand to the limits to force many errors from that wing. However, that wasn't enough to keep him safe, losing energy in the decider to propel world no.
1 over the top. Federer served at 53% but experienced only two loose service games in the set he lost, with Novak unable to reach at least a deuce in the remaining return games! The pressure was on the Serb in sets one and three, and he couldn't endure it, getting broken three times from 11 chances offered to Federer to finish his journey in the first round despite a solid effort.
The Swiss had a 22-14 advantage in service winners, and a 25-20 in the winners from the field department, creating a buffer that kept him safe from those 20 forced errors he committed, with nothing to separate them in the area of the unforced mistakes.
Roger had a massive 52-39 advantage in the shortest rallies up to four strokes thanks to those service winners, earning his victory there as Djokovic stayed in touch in the mid-range exchanges and had a 10-6 lead in the most extended ones.
Novak Djokovic lost to Roger Federer in their first match in Monte Carlo 2006.
Federer converted the fifth break chance to gain an early advantage in the third game and delivered another break at 5-3 to secure the opener in 33 minutes.
Playing on a much higher level in set number two, Novak broke Roger in games three and seven, serving well and dominating from the baseline to clinch the set 6-2 and become the favorite if he would keep that pace. Still, the youngster started to struggle physically, spraying more errors in the third set's second game than in the entire second set to give serve away, unable to find his best tennis and allowing Roger to seal the deal with a hold at 5-3.
"I'm delighted with the way I played against Roger today. On the other hand, I'm a little disappointed because I knew I had a chance to beat him. A couple of points decided the winner, and I had the opportunity to prevail.
Federer played his first match on clay this year, while I already scored two qualifying victories. Anyway, it was a significant experience for me, and my confidence will grow now, knowing that I played on a high level. I'm still young, and I need more encounters like this one to learn how to play against the rivals from the top," Novak Djokovic said.