How the drop-in file works
Current Debian and Ubuntu ship an /etc/ssh/sshd_config whose first effective line is Include /etc/ssh/sshd_config.d/*.conf. Files in that directory are read at that point, before the rest of the main file.
That ordering matters, because for most keywords sshd keeps the first value it reads. A drop-in only wins because it is included near the top; a file appended to the bottom of sshd_config would lose to the values above it. Naming the file with a number prefix, such as 99-hardening.conf, controls its order relative to other drop-ins your distribution or your cloud image may already have installed.
Everything after a Match line belongs to that block, so the generated file always places Match blocks at the very end.