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Date
Winner
Loser
Tournament
Round
Score
2019-04-08
Taro Daniel (75)
Adrian Menendez Maceiras (139)
Marrakech
R16
6-2 1-6 6-1
2019-04-08
Adrian Menendez Maceiras (139)
Fernando Verdasco (38)
Marrakech
R32
5-7 6-2 6-2
2019-02-11
Christopher Eubanks (166)
Adrian Menendez Maceiras (121)
New York
R32
6-4 7-6(4)
2019-02-04
Jeremy Chardy (35)
Adrian Menendez Maceiras (124)
Montpellier
R32
6-1 6-1
2018-09-17
Denis Shapovalov (34)
Adrian Menendez Maceiras (126)
St. Petersburg
R32
7-6(3) 6-2
2018-07-23
Jaume Munar (89)
Adrian Menendez Maceiras (149)
Gstaad
R32
6-1 6-0
2018-02-12
Adrian Mannarino (25)
Adrian Menendez Maceiras (128)
New York
QF
7-5 2-6 6-3
2018-02-12
Adrian Menendez Maceiras (128)
Jeremy Chardy (95)
New York
R16
7-5 7-6(5)
2018-02-12
Adrian Menendez Maceiras (128)
Steve Johnson (49)
New York
R32
1-6 6-3 7-6(7)
2018-02-05
Corentin Moutet (152)
Adrian Menendez Maceiras (131)
Quito
R32
6-4 6-7(5) 6-2
2017-09-25
Dusan Lajovic (84)
Adrian Menendez Maceiras (133)
Chengdu
R32
6-3 7-6(3)
2017-08-28
Juan Martin del Potro (28)
Adrian Menendez Maceiras (148)
US Open
R64
6-2 6-3 7-6(3)
2017-08-28
Adrian Menendez Maceiras (148)
Patrick Kypson (923)
US Open
R128
6-4 7-6(9) 6-1
2017-07-17
Pierre Hugues Herbert (72)
Adrian Menendez Maceiras (140)
Newport
R16
7-5 2-6 6-3
2017-07-17
Adrian Menendez Maceiras (140)
Stefan Kozlov (129)
Newport
R32
6-2 7-6(5)
2017-05-01
Jordan Thompson (91)
Adrian Menendez Maceiras (175)
Istanbul
R32
6-7(4) 6-0 6-0
2015-07-20
Bernard Tomic (29)
Adrian Menendez Maceiras (116)
Bogota
R16
6-7(5) 6-2 6-4
2015-07-20
Adrian Menendez Maceiras (116)
Alejandro Gonzalez (115)
Bogota
R32
4-6 6-4 7-6(9)
2015-07-13
Alejandro Falla (122)
Adrian Menendez Maceiras (114)
Newport
R32
6-1 7-5
2015-03-25
Tim Smyczek (75)
Adrian Menendez Maceiras (126)
Miami Masters
R128
4-6 6-3 6-4
2015-02-02
Paolo Lorenzi (68)
Adrian Menendez Maceiras (130)
Quito
R32
4-6 6-4 7-6(1)
2013-02-04
Benoit Paire (43)
Adrian Menendez Maceiras (207)
Montpellier
R32
6-0 6-2
2013-01-14
Jeremy Chardy (36)
Adrian Menendez Maceiras (233)
Australian Open
R128
7-6(5) 6-7(3) 6-2 6-1
2012-06-25
Michael Russell (112)
Adrian Menendez Maceiras (212)
Wimbledon
R128
6-3 6-1 7-6(7)