Something seems to be wrong with the hyperlink.

I get a message saying that “I Cry Out.musx” does not exist.

https://www.dropbox.com/s/hqh4hlbi6yumacy/I%20Cry%20Out.musx?dl=0 

try this one

… When I check repeats, the sequence seems to be correct …

If I understand you correctly, your words “… I check repeats …” mean this:

Repeat Tool.

Repeat menu > Check Repeats…

- right?

When I do so in your Finale document, I get the playback route “1–81”, i. e. playing through all the measures 1 to 81 without repeating anything.

Is “1–81” the correct playback sequence?

Or do you need another playback route?

By The Way:

In the top of the Repeat menu you have the commands

Create Simple Repeat

and

Create First and Second Ending

which seem to create repeats, that play back.

I want it to play the repeats just as they are scored. It seems to only play 1-81 on my end. 

I have some ideas for you.

Open your Finale document (= I Cry Out).

1) Document menu > Playback/Record Options…

Make sure that the settings are as needed.

I would select the four Play options, and I would de-select Ignore Repeats.

2) Try playing the document with Human Playback off.

3) Also try this:

MIDI/Audio menu > Play Finale Through MIDI

4) Also, you could set the Playback Region to go from Measure 1, instead of from Leftmost Measure.

However, I am using Mac Finale, and I do not hear anything wrong in the playback.

Your issues may be specific for Windows Finale.

Go to Playback Settings > Playback/Record Options > uncheck ignore repeats (it was checked ...) > OK > OK,  then all repeats  play back correctly

I got it to work be hitting "reset repeats" in the playback/Record Options dialogue. Thanks to all for trying. 

Michael Pickett Thank you! This has fixed the issue for me, two years after you posted it :)