Iron Man, Vol. 1 #44 (1972)

Weep For A Lost Nightmare
As his previous attacks by Slasher, Demitrius, and Mikas were unsuccessful, Mister Kline changes tactics and sends an android duplicate of the Night Phantom after Iron Man, who is still recovering from the last battle. Meanwhile, Kevin O'Brien is starting to like the power he has in the Guardsman suit.
Release Date: 1972