JustCooLpOOLe You might take this opportunity on the GTM to perform a tcpdump to see what you are receiving back from the destination. The following should be a close enough syntax and you can change the port if it's HTTPS rather than HTTP.
tcpdump -nni 0.0:nnp host <gtm_ip> and host <destination_IP> and port 80
It is common that sometimes a curl will function slightly different than the health monitor. A good example of this is I was able to perform a curl from my lab LTM to my lab apache server and the response was the one I expected but when I did a very similar request using the health monitor it would fail because the server said it was not able to find the destination that I requested. I ended up having to add in an entry that allowed the server to respond to any request to itself on 80 which I later narrowed it down once I came up with a lab root domain to use.