Can you post the self-hosted Wireguard config file (with the keys redacted)? What is the IP address that it assigns to the client and does it assign a DNS to the client?
If I understand your network setup correctly, the Wireguard config may be assigning the client with IP address 10.13.37.x. The pi-hole has IP address 10.13.37.50 and is on the LAN side of the router, so it is not reachable because the router VPN client goes through the WAN side. Tethering is on the WAN side and DNS 10.13.37.50 is shown on your “Tethering” screenshot.
The android cellphone and laptop may be working because they are on the LAN side of the router, so the the pi-hole on the LAN side is reachable.