Woody met the Turtles for the first time in the year, that Leonardo, Donatello and Michelangelo were still looking for their lost brother Raphael. Looking for something to eat, Michelangelo ransacked through the dumpster at the back door of Rupert's Pizzeria, but was surprised by Woody. However, instead of running away in panic at the sight, Woody liked this strange creature and gave them a fresh Pizza. A deep friendship between him and the Turtles, in particular with the sociable Michelangelo (who Woody often calls Mikester) was born.
Since that time the Turtles came regularly to Rupert's and were supplied by Woody with fresh pizza, and after his brothers had found him, Woody also presented Raphael with pizza. However, this good relationship came to an abrupt end after the mutantSlash had broken out from the laboratory of StockGen and made the roads unsafe and one night ambushed Woody shortly after Michelangelo had again paid him a visit. Although Woody was only slightly injured in the attack, the shock inflicted such a severe trauma that he decided to never again directly do anything with the Turtles. After he had somewhat recovered from the horror, Woody got remorseful that he had just simply dropped his friend, and later he helped Michelangelo with an important note, when he sought the Foot Clan who had brought his brother Leonardo under their power.
Woody Dirkins is named after IDW's head of marketing Dirk Wood. He is also drawn to resemble him.