Murray admitted that the most "awkward" moment training with Djokovic was when he was "in a lot of pain."

At the close of 2024, Murray formed a partnership with his longtime competitor Djokovic, shocking the tennis community. Their collaboration peaked at the 2025 Australian Open when Djokovic overcame Alcaraz, marking one of the few highlights of their time working together.

Djokovic’s unlucky injury in the Australian Open semifinal completely altered the situation, and their partnership never resumed. According to BBC, Murray later shared his true feelings, expressing regret but also acknowledging the valuable lessons he learned from the experience.

Murray said, “What happened in Australia and the injury was unfortunate, but I saw him play some incredibly impressive tennis during that tournament. After the injury, it was definitely a tough few months for him, but it was hard for the team and all of us as well. I was disappointed that maybe he didn’t achieve the results I hoped for, but I gained a lot of knowledge about coaching.”

He knew from the start that taking on this role meant working with one of the greatest athletes in history, which made it a highly challenging task, especially given Djokovic’s well-known intensity and dedication to tennis. Murray still views the experience positively, considering it an amazing journey that taught him valuable coaching insights. However, the former British star also shared his feelings from their first training session together.

Their initial collaboration as coach and player didn’t begin on the court but on the running track. Murray described running alongside Djokovic, which seemed like a simple task but turned out to be far more complicated than expected for the former world number one.

After just a few minutes of running, Murray’s post-retirement fitness sharply contrasted with that of his former rival. “I couldn’t say anything at the time because after 4 or 5 minutes it was just too awkward. Anyway, I managed to finish the 50 minutes, but I was in a lot of pain. I told his team, ‘Guys, you’ve got to help me, I ran for 45 minutes and my left calf cramped up,’” Murray said on The Tennis Podcast.

At that moment, his biggest concern wasn’t the pain but how Djokovic might perceive his condition. He continued, “I just felt I couldn’t stop. I didn’t want him to think, ‘Wow, this is the guy who’s been competing against me for years, and he can’t last five minutes in training.’ So I pushed through, but it was really an extremely awkward moment for me.”

This anecdote also hinted at the unique and somewhat awkward atmosphere during their brief partnership at the 2025 Australian Open. Their first official match wasn’t an ideal start, with Djokovic appearing frustrated and underperforming against a lower-ranked opponent. Nevertheless, despite the rocky beginning, there were still some memorable highlights during Murray’s coaching tenure.

Djokovic praised Murray’s exceptional tennis intellect and acknowledged the valuable guidance he provided during matches. As a former rival, Murray offered a unique perspective, and the Brit also “learned a lot about coaching.”

Their collaboration’s peak was undoubtedly the 2025 Australian Open quarterfinal, where Djokovic came back from a set down to beat Alcaraz 4-6, 6-4, 6-3, 6-4. Murray described this match as “one of the best matches I have watched live.” Ultimately, their partnership remained short-lived. After Djokovic retired injured in the Australian Open semifinal, they mutually decided to end their cooperation in May 2025.

Djokovic admitted that the outcome was not what they had hoped for but emphasized that he “really enjoyed the time” and felt their relationship had grown stronger.(Source: Tennis Home, Author: Spark)