The Chicago Match Cup is the second stop on the USA Match Racing Grand Slam, and will be held at the Chicago Yacht Club from 19th–21st August.

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 Overall placings 
1. AUS Harry Price, Ben Robinson, Murray Jones
2. USA Steven Lowery, Rory Lewis, Maurin Lovera
3. USA Peter Holz, Mike Whitford, Will Holz
4. USA David Storrs, Chris Steele, Shane Diviney
5. MAS Jeremy Koo, Graeme Sutherland, Mohd Salfullah Mond Esa
6. GBR Connor Miller, Mark Davies, Isaac Clarke
7. MEX Hector Guzman, Hector Guzman Sr., Aisling Sullivan
8. USA James Wagner, David Wagner, Spencer Keenan
Final 1 2 3 4 5 W
Harry Price Harry Price, AUS 1 1 1 3
Steven Lowery Steven Lowery, USA 0 0 0 0
Petit Final 1 2 3 W
David Storrs David Storrs, USA 0 1 0 1
Peter Holz Peter Holz, USA 1 0 1 2
Semi Final 1 1 2 3 4 5 W
Harry Price Harry Price, AUS 1 1 1 3
Peter Holz Peter Holz, USA 0 0 0 0
Semi Final 2 1 2 3 4 5 W
David Storrs David Storrs, USA 0 0 0 0
Steven Lowery Steven Lowery, USA 1 1 1 3
Round Robin 2 David Storrs, USA Harry Price, AUS Jeremy Koo, MAS Peter Holz, USA Steven Lowery, USA Connor Miller, GBR Hector Guzman, MEX James Wagner, USA W %
David Storrs David Storrs, USA 1 1 0 0 1 1 1 5 71%
Harry Price Harry Price, AUS 0 1 1 0 1 1 1 5 71%
Jeremy Koo Jeremy Koo, MAS 0 0 0 1 0 0 1 2 29%
Peter Holz Peter Holz, USA 1 0 1 0 0 1 1 4 57%
Steven Lowery Steven Lowery, USA 1 1 0 1 1 1 1 6 86%
Connor Miller Connor Miller, GBR 0 0 1 1 0 0 1 3 43%
Hector Guzman Hector Guzman, MEX 0 0 1 0 0 1 1 3 43%
James Wagner James Wagner, USA 0 0 0 0 0 0 0 0 0%
Round Robin 1 David Storrs, USA Harry Price, AUS Jeremy Koo, MAS Peter Holz, USA Steven Lowery, USA Connor Miller, GBR Hector Guzman, MEX James Wagner, USA W %
David Storrs David Storrs, USA 0 1 0 1 1 1 1 5 71%
Harry Price Harry Price, AUS 1 0 0 1 1 1 1 5 71%
Jeremy Koo Jeremy Koo, MAS 0 1 0 1 1 1 1 5 71%
Peter Holz Peter Holz, USA 1 1 1 1 0 0 1 5 71%
Steven Lowery Steven Lowery, USA 0 0 0 0 1 1 1 3 43%
Connor Miller Connor Miller, GBR 0 0 0 1 0 1 1 3 43%
Hector Guzman Hector Guzman, MEX 0 0 0 1 0 0 1 2 29%
James Wagner James Wagner, USA 0 0 0 0 0 0 0 0 0%