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Date
Winner
Loser
Tournament
Round
Score
2023-04-10
Novak Djokovic (1)
Ivan Gakhov (198)
Monte Carlo Masters
R32
7-6(5) 6-2
2023-04-10
Ivan Gakhov (198)
Mackenzie Mcdonald (52)
Monte Carlo Masters
R64
7-6(6) 2-6 6-3
2022-07-25
Yannick Hanfmann (140)
Ivan Gakhov (315)
Kitzbuhel
R16
6-3 6-7(5) 6-4