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Date
Winner
Loser
Tournament
Round
Score
2024-05-20
Hailey Baptiste (99)
Valentini Grammatikopoulou (286)
Roland Garros
QF
3-6 6-4 6-3
2024-04-12
J. C. Svendsen (0)
Valentini Grammatikopoulou (286)
Billie Jean King Cup - Group I
RR
7-6 4-6 6-3
2024-04-11
Valentini Grammatikopoulou (286)
Daniela Vismane (389)
Billie Jean King Cup - Group I
RR
0-6 5-7
2024-04-10
Valentini Grammatikopoulou (286)
E. Sartz-Lunde (0)
Billie Jean King Cup - Group I
RR
6-3 2-6 6-4
2024-04-09
Mia Ristic (304)
Valentini Grammatikopoulou (286)
Billie Jean King Cup - Group I
RR
2-6 6-4 6-1
2024-04-08
C. W. Hennemann (0)
Valentini Grammatikopoulou (286)
Billie Jean King Cup - Group I
RR
6-4 3-6 6-4
2024-01-10
Dayana Yastremska (27)
Valentini Grammatikopoulou (286)
Australian Open
SF
6-4 3-6 6-4
2024-01-09
Valentini Grammatikopoulou (286)
Elvina Kalieva (301)
Australian Open
QF
7-5 6-3
2023-07-24
Dalila Jakupovic (267)
Valentini Grammatikopoulou (170)
Lausanne
R32
7-6(11) 6-2
2023-07-17
Tamara Korpatsch (99)
Valentini Grammatikopoulou (170)
Budapest
R32
6-4 6-4
2023-04-15
Valentini Grammatikopoulou (202)
Elena Malygina (374)
BJK Cup G2 PPO: EST vs GRE
RR
6-2 6-4
2023-04-14
Valentini Grammatikopoulou (202)
Matilde Jorge (629)
BJK Cup G2 RR: GRE vs POR
RR
6-3 6-2
2023-04-13
Valentini Grammatikopoulou (202)
Dea Herdzelas (357)
BJK Cup G2 RR: GRE vs BIH
RR
6-1 1-0 RET
2023-04-12
Valentini Grammatikopoulou (202)
Elaine Genovese ()
BJK Cup G2 RR: GRE vs MLT
RR
6-1 6-2
2023-04-11
Valentini Grammatikopoulou (202)
Mika Buchnik (853)
BJK Cup G2 RR: GRE vs ISR
RR
6-2 6-0
2023-01-02
Lucia Bronzetti (54)
Valentini Grammatikopoulou (199)
United Cup
SF
6-2 6-3
2022-05-23
Daria Saville (127)
Valentini Grammatikopoulou (187)
Roland Garros
R128
6-1 6-2
2021-08-30
Elise Mertens (16)
Valentini Grammatikopoulou (234)
US Open
R64
6-2 6-2
2021-08-30
Valentini Grammatikopoulou (234)
Anna Blinkova (84)
US Open
R128
6-3 6-2
2021-07-12
Jasmine Paolini (87)
Valentini Grammatikopoulou (273)
Lausanne
R32
6-3 4-6 7-5
2021-01-06
Alize Cornet (53)
Valentini Grammatikopoulou (269)
Abu Dhabi
R64
6-2 6-2
2020-02-08
Isabella Shinikova (165)
Valentini Grammatikopoulou (301)
Fed Cup G1 REL: BUL vs GRE
RR
6-3 6-1
2020-02-06
Valentini Grammatikopoulou (301)
Sinja Kraus (869)
Fed Cup G1 RR: AUT vs GRE
RR
6-4 6-4
2020-02-05
Valentini Grammatikopoulou (301)
Elena Malygina (553)
Fed Cup G1 RR: EST vs GRE
RR
6-4 4-6 7-6(8)
2019-02-09
Berfu Cengiz (331)
Valentini Grammatikopoulou (171)
Fed Cup G1 PM: GRE vs TUR
RR
5-3 RET
2019-02-08
Valentini Grammatikopoulou (171)
Kaja Juvan (169)
Fed Cup G1 RR: GRE vs SLO
RR
7-6(2) 5-7 6-3
2019-02-07
Katie Boulter (83)
Valentini Grammatikopoulou (171)
Fed Cup G1 RR: GBR vs GRE
RR
6-3 4-6 6-3
2019-02-06
Dalma Galfi (311)
Valentini Grammatikopoulou (171)
Fed Cup G1 RR: HUN vs GRE
RR
6-0 6-3
2018-10-15
Anastasia Pavlyuchenkova (40)
Valentini Grammatikopoulou (170)
Moscow
R16
7-5 6-0
2018-10-08
Kristyna Pliskova (97)
Valentini Grammatikopoulou (171)
Linz
R32
6-4 6-2
2018-07-23
Varvara Flink (318)
Valentini Grammatikopoulou (181)
Moscow
R32
6-2 3-6 6-3
2018-06-11
Aleksandra Krunic (55)
Valentini Grammatikopoulou (179)
s-Hertogenbosch
R32
6-1 6-0
2018-04-21
Eleonora Molinaro (450)
Valentini Grammatikopoulou (171)
Fed Cup G2 PPO: GRE vs LUX
RR
6-3 3-6 6-4
2018-04-20
Valentini Grammatikopoulou (171)
Clara Tauson (729)
Fed Cup G2 RR: DEN vs GRE
RR
6-7(3) 7-6(4) 6-0
2018-04-19
Valentini Grammatikopoulou (171)
Dona Abo Habaga ()
Fed Cup G2 RR: EGY vs GRE
RR
6-2 6-3
2018-04-09
Johanna Larsson (73)
Valentini Grammatikopoulou (183)
Bogota
R16
4-6 6-4 6-4
2018-04-09
Valentini Grammatikopoulou (183)
Miyu Kato (138)
Bogota
R32
5-7 6-4 6-4
2018-04-02
Jana Fett (109)
Valentini Grammatikopoulou (185)
Monterrey
R32
6-0 6-2
2017-10-09
Nicole Gibbs (114)
Valentini Grammatikopoulou (207)
Hong Kong
R32
4-6 6-2 7-5
2017-07-31
Sabine Lisicki (190)
Valentini Grammatikopoulou (179)
Washington
R32
7-6(7) 7-6(5)
2017-04-17
Qiang Wang (68)
Valentini Grammatikopoulou (196)
Zhengzhou
R16
4-6 7-5 6-2
2017-04-17
Valentini Grammatikopoulou (196)
Yi Fan Xu (378)
Zhengzhou
R32
6-1 6-3
2014-02-08
Valentini Grammatikopoulou (556)
Jane Fennelly ()
Fed Cup G3 PO: GRE vs IRL
RR
6-2 6-0
2014-02-07
Valentini Grammatikopoulou (556)
Anastasia Detiuc ()
Fed Cup G3 RR: GRE vs MDA
RR
6-1 6-0
2014-02-05
Valentini Grammatikopoulou (556)
Eliza Omirou ()
Fed Cup G3 RR: GRE vs CYP
RR
6-0 6-0