Like every other champion, Novak Djokovic has experienced countless highs and lows throughout his legendary career. However, one match continues to stand out as his most painful setback.
Djokovic's most heartbreaking loss of his career came at the 2016 Rio Olympics when Juan Martin del Potro bested him 7-6, 7-6 in the first round after two hours and 27 minutes.
The draw linked two good friends at the start of the event, and the Argentine took the crucial points to secure a memorable victory and crush the Serb's Olympic gold medal dreams.
¡Épica victoria de Delpo! 👏 😍
Recordamos el emotivo triunfo de 🇦🇷 Del Potro (7-6 y 7-6) frente a 🇷🇸 Djokovic (N° 1) en #Rio2016.
El argentino volvía de una lesión de 14 meses, ocupaba el puesto 141 del ránking y recibió una ovación en Brasil @teamdelpopic.twitter.com/SLu2wVWwQU
— Golpe de Tenis (@golpedetenis) April 1, 2020
Djokovic entered his third Olympic Games tournament as the favorite and at the very peak of his powers. A couple of months earlier, he achieved the rare "Djokovic Slam" by holding all four Major titles.
He wished to go all the way in Rio and earned Olympic glory, but it was not to be for the 29-year-old. Despite injuries and setbacks, del Potro still possessed the firepower to rise on the big stage.
The crowd cheered for Novak, but Juan Martin produced one of his most inspired performances that would lead him toward a medal. It was a devastating loss for the world's best player and the one he hardly accepted.
Novak Djokovic & Juan Martin del Potro, 2016 Rio Olympics© Stream screenshot
The Olympics had always carried special meaning for Novak, especially after taking the bronze medal in Beijing and missing it in London four years later. Rio should have been his event, but it ended up with a painful early loss.
It remains the darkest moment of his career, a reminder of how even at the summit, dreams can crumble in an instant.
"The worst match of my career was at the 2016 Rio Olympics against Juan Martin del Potro. It was a very emotional duel, and I remember the support of the entire stadium.
I was at the peak of my career, coming off four consecutive Major titles and feeling like it was my opportunity to claim the Olympic gold medal," Novak Djokovic said.
