Marin Cilic (CRO) vs. Tennys Sandgren (USA) – The 2014 champion may be a dark horse here despite being the 5th seed and having won 6 matches at Wimbledon.
 Alexander Zverev (GER) vs. [Q] Darian King (BAR) – Can Zverev handle the spotlight? If so, the Montreal and Washington, DC champion could go really far here.
LOUIS ARMSTRONG STADIUM
 John Isner (USA) vs. Pierre-Hugues Herbert (FRA) – I predict at least 2 tiebreak sets.
 Jack Sock (USA) vs. Jordan Thompson (AUS)
Steve Johnson (USA) vs. Nicolas Almagro (ESP) – I give a slight edge to Johnson based upon his solid 2017 and a home crowd edge. Still, this could be close to 50-50 if Almagro is healthy and dialed into the match.
 Sam Querrey (USA) vs. Gilles Simon (FRA) – One of the first matches I covered with press credentials was their 2008 semifinal clash in Indianapolis (Simon won). Querrey has had a massive 2017 campaign, but he could lose this match (and a lot of momentum).
 Jo-Wilfried Tsonga (FRA) vs. Marius Copil (ROU)
[PR] Thanasi Kokkinakis (AUS) vs. Janko Tipsarevic (ROU) – I have no idea due to the health issues surrounding each player. I think experience helps …
 Kevin Anderson (RSA) vs. [Q] JC Aragone (USA) – Anderson has rebounded nicely from some injury issues.
 Lucas Pouille (FRA) vs. [Q] Ruben Bemelmans (BEL) – He is not in the same form he was last year, but he could do well.
 Robin Haase (NED) vs. [Q] Kyle Edmund (GBR)
 Gilles Muller (LUX) vs Bernard Tomic (AUS) – This is an interesting match, but I feel pretty good about Muller’s chances.
Horacio Zeballos (ARG) vs. Hyeon Chung (KOR)
 Karen Khachanov (RUS) vs Yen-Hsun Lu (TPE)
[Q] Radu Albot (MDA) vs. Ernesto Escobedo (USA)
Jared Donaldson (USA) vs. Nikoloz Basilashvili (GEO)
Benoit Paire (FRA) vs [LL] Lukas Lacko (SVK)
Dudi Sela (ISR) vs [WC] Christopher Eubanks (USA)
 David Ferrer (ESP) vs [Q] Mikhail Kukushkin (KAZ)
[Q] Denis Shapovalov (CAN) vs. D. Medvedev (RUS) – This will be interesting.
[PR] Ernests Gulbis (LAT) vs Alessandro Giannessi (ITA) – With Gulbis, I never have any idea.
[Q] Marton Fucsovics (HUN) vs. [Q] Nicolas Mahut (FRA)
 Albert Ramos-Vinolas (ESP) vs Denis Istomin (UZB)
Jiri Vesely (CZE) vs. Borna Coric (CRO) – Coric did not show me enough grit in Montreal so I will go with the Czech.
 Pablo Carreno Busta (ESP) vs [Q] Evan King (USA)
 Diego Schwartzman (ARG) vs. Carlos Berlocq (ARG)
Rogerio Dutra Silva (BRA) vs Florian Mayer (GER)
 Mischa Zverev (GER) vs [WC] Thai-Son Kwiatkowski (USA)
[PR] Dmitry Tursunov (RUS) vs [Q] Cameron Norrie (GBR) – I am glad Tursunov is still plugging away, but I think his best tennis days are behind him.
Thomas Fabbiano (ITA) vs [Q] John-Patrick Smith (AUS)
[PR] Andreas Haider-Maurer (AUT) vs. Evgeny Donskoy (RUS)
Joao Sousa (POR) vs. Paolo Lorenzi (ITA) – This is a 50-50 match in my view.