The winger struck in the 53rd and 79th minutes - either side of a Kevin Nolan equaliser - to ensure Chris Hughton's Newcastle failed one of the acid tests of life in the Coca-Cola Championship - a wet Tuesday at Glanford Park.
Newcastle's winless run now stands at four games, and this defeat, 13 years to the day after Kevin Keegan's swashbuckling side famously beat Manchester United 5-0, shows just how much work the club's modern day players have to do if they are to ever scale those heights again.
Scunthorpe opened the scoring 53 minutes in when Zurab Khizanishvili, facing his own goal, allowed himself to be shrugged off the ball by Gary Hooper, who unselfishly squared for former York winger Woolford.
Geremi could have brought his side level moments later when he lashed over, but Nolan showed him how to do it with 25 minutes to go as he grabbed his seventh goal of the season. It was a picture-book goal for Nolan, as he arrived right on time on the edge of the area to hammer home into the bottom corner after a storming break from Danny Guthrie had created the chance.
Nolan again went close with a diving header after Ryan Taylor's cross, but rather than sit back and defend a point, Scunthorpe pressed for a winner which duly arrived 11 minutes from the end when Woolford got on the end of Sam Togwell's header to waltz through Newcastle's absent defence before leaving Steve Harper with no chance.