Following tools will help you detecting outdated software.
After updating from Linux Mint 18.3 to 19, wine stopped working. This is what was required to correct.
sudo all below commands if required
dpkg --add-architecture i386
apt-add-repository 'deb https://dl.winehq.org/wine-builds/ubuntu/ bionic main'
wget -nc https://dl.winehq.org/wine-builds/Release.key
apt-key add Release.key
Check if you do not have duplicate lines from an earlier install.
Then the final step.
apt-get install --install-recommends winehq-stable
Source: Ubuntu – WineHQ Wiki