The Serbian star had captured their last four meetings since the Russian ended his bid for a rare calendar Grand Slam at the 2021 US Open final.
Novak Djokovic’s 20-match win streak and the perfect start to 2023 came to an end on Friday when Daniil Medvedev won their Dubai Championship semi-final in straight sets.
Medvedev came through 6-4, 6-4, and will face Russian compatriot Andrey Rublev, the defending champion, in Saturday’s final.
World number one Djokovic had been undefeated since claiming the season-ending ATP Finals in November.
He then went on to clinch the Adelaide title and a 10th Australian Open for a record-equalling 22nd Grand Slam crown.
However, Medvedev is also on a hot streak and arrived in the Gulf with titles in Rotterdam and Doha.
The world number seven has now racked up 13 successive wins after claiming just his fifth victory in 14 meetings against Djokovic.
The Serbian star had captured their last four meetings since the Russian ended his bid for a rare calendar Grand Slam at the 2021 US Open final.
On Friday, the 27-year-old Medvedev fired eight aces in his 27 winners. Djokovic committed 14 unforced errors, twice as many as his opponent in the 95-minute semi-final.
Earlier, Rublev defeated Germany’s Alexander Zverev for the first time in six meetings with a 6-3, 7-6 (11/9) victory.