I managed to solve this issue by running
/Applications/MAMP/bin/php/php5.4.4/bin/pecl install xdebug
At first I was seeing issues with the Zend API number using pecl. I followed this post: pecl installs for previous php version and set the following:
sudo /Applications/MAMP/bin/php/php5.4.4/bin/pear config-set php_ini /Applications/MAMP/bin/php/php5.4.4/conf/php.ini
sudo /Applications/MAMP/bin/php/php5.4.4/bin/pecl config-set bin_dir /Applications/MAMP/bin/php/php5.4.4/bin/
Not sure if these configs had something to do with it failing before