Ultimate Marvel Team-Up #6 (2001)

Spider-Man & Punisher
Frank Castle is in prison along with several of the people he targets. When he hears an inmate planning to commit a rape that was interrupted by Daredevil, he kills the man, and ends up in solitary confinement under restraints. The restraints do not prevent him from keeping the cup, pen and paperclip his lawyer left behind, however, which provides him with the tools he needs to make good his escape.
Release Date: 2001