I had just went to the range a few weeks ago and was using UMC rounds for just plinking. I went through 100rds without issue but the accuracy was fubar. It was suggested I try WWB 9mm so I went to wal-mart and got a value pack. During my next trip to the range I had 8 times where a shell failed to eject and was stuck in the chamber. I was able to drop the mag and clear the shell and continue on but this is the first time I've had this issue.

Is this a known issue with the winchester rounds or is there something else I should be looking at?

Quoted: I had just went to the range a few weeks ago and was using UMC rounds for just plinking. I went through 100rds without issue but the accuracy was fubar. It was suggested I try WWB 9mm so I went to wal-mart and got a value pack. During my next trip to the range I had 8 times where a shell failed to eject and was stuck in the chamber. I was able to drop the mag and clear the shell and continue on but this is the first time I've had this issue. Is this a known issue with the winchester rounds or is there something else I should be looking at?

Sounds like bad ammo. try something else.

How many rounds do you have through the pistol?  S&W are known for chipped extractors, check that first.  Try other ammo.  

The best guess on round count would be around 600-700.

I did an inspection and didn't see anything wrong with the extractor

It's not ammo. Something is wrong with the gun. I shoot WWB and UMC all the time in mine with no problems.

Look at your extractor and make sure it is free of chips and clean behind it. Next have a gun smith check and repair as needed.

I sent my 5904 back to Smith & Wesson and they repaired mine for no cost; including repairing the rear sight.  I like sending mine to the factory for a real tune-up.