A few questions:
1) Is this a local or cloud printer?
2) Is the "Print" button you are referring to the one in the PDF viewer, Chrome's Print Preview, or the Windows system dialog?
3) By advanced print settings, do you mean the Print Preview "Advanced options" dialog for cloud printers or something else?
4) What are you using to select paper size, orientation and tray setting? Print Preview, the system dialog, the printer settings in Windows, or some combination of those?

Here's some answers:

1) This is a local printer, connected via USB.
2) I'm referring to Chrome's Print Preview button.
3) When you click on Chrome's Print Preview button, it shows a bunch of options. One of those options is "Print Using System Dialog." Those are the advanced options I'm referring to.
4) After selecting "Print Using System Dialog," click the button "Preferences." That is where I'm selecting paper size, orientation and tray setting.

Thank you for providing more feedback. Adding the requester to the cc list.

For more details visit https://www.chromium.org/issue-tracking/autotriage - Your friendly Sheriffbot

Able to reproduce the issue on chrome reported version 67.0.3396.87 and latest chrome 69.0.3466.0 using Windows-7 with the file attached in comment# 0. As this issue is seen from M-60(60.0.3112.0), hence considering this issue as Non-Regression and marking it as Untriaged.

Note: Unable to confirm the behaviour on Mac and Linux, as we don't have printer setup here for Mac and Linux.

Thanks!

This could be related to a couple of different known issues, or some combination of the two.

First, the PDF you attached is portrait oriented, so Chrome will automatically rotate it to match the paper size that is selected in Print Preview (see https://crbug.com/98641). So if the paper size is landscape oriented, it will be rotated 90 degrees.

Second, on Windows the PDF from Print Preview gets sent to the system dialog, not the original PDF (see https://crbug.com/700181). This can create possibly unexpected effects when setting various settings in the system dialog. A workaround here is to use the system dialog directly by using ctrl + shift + P instead of using the print preview button.

To determine which of these issues might be going on, a couple more questions:
1) What paper size is listed as the selected paper in the Print Preview dialog, and what is its orientation? For orientation, as an example, XPS Document Writer has both a "Letter" and a "Letter Rotated" paper size. The former is portrait oriented (8.5 x 11) and the latter is landscape (11 x 8.5).

2) Do you happen to know the orientation of the Letter #10 paper in the system dialog?

3) If you print with the system dialog directly as mentioned above, does the PDF print as expected?

Here's some more answers:

1) The default that shows up in the Print Preview dialogue is "Letter" (8.5 x 11) and "Portrait."

2) When I select "Letter #10" in the system dialog, it defaults to Portrait still.

3) If I print with the system dialog directly as you asked, I still get incorrect behavior, printing in portrait.