I think i have the same issue.
Ubuntu 18.04.5 i386 with two NIC and configured in order to listen and serve 
lease on a specific NIC.

After the boot procedure, the service fail.
If i make a restart without changing anything it's work.

** Attachment added: "status-restart.txt"
   
https://bugs.launchpad.net/ubuntu/+source/isc-dhcp/+bug/1772941/+attachment/5444319/+files/status-restart.txt

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https://bugs.launchpad.net/bugs/1772941

Title:
  isc-dhcp-server does not listen network interfaces

Status in isc-dhcp package in Ubuntu:
  Confirmed

Bug description:
  System: Ubuntu 16.04.4 LTS x64 XFCE desktop
  Version of package: isc-dhcp-server
  Uname: 4.4.0-127-generic
  Result spected: service isc-dhcp-server status returning that service is 
active, running and OK.
  Network interfaces: 2, enp0s3 (static, main), en0s8 not configured yet.
  Current result:
  service isc-dhcp-server status returns an error message, which says that 
there is no network interface listening.

  In /etc/default/isc-dhcp-server I have configured this line:
  INTERFACES="enp0s3" but still giving the same error. Links to an ask ubuntu 
question:https://askubuntu.com/questions/536531/dhcp-server-wont-start-gives-not-configured-to-listen-on-any-interfaces-eve

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