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Date
Winner
Loser
Tournament
Round
Score
2024-01-14
Emil Ruusuvuori (87)
Patrick Kypson (157)
Australian Open
R128
6-4 3-6 4-6 6(4)-7(7)
2023-05-29
Radu Albot (113)
Patrick Kypson (329)
Roland Garros
R128
6-3 6-2 4-6 6-1
2017-08-28
Adrian Menendez Maceiras (148)
Patrick Kypson (923)
US Open
R128
6-4 7-6(9) 6-1