HI there,
NO, It won’t… You need to look at this thread on the Holes, they need to be ovals & plated through #1, The tip of the iron will fit down to contact the battery pads. Also use solder paste on the Xiao pads prior to placing it and use a clamp. Check the thread for more.
I get 100% on using this tech. Even the Xiao Relay board has added this to their solder mask.
Or like this… 
HTH
GL 
PJ 