Simone Pepe and Amauri were the guilty ones...
The Rossoneri had gone ahead in the 21st minute thanks to a wonderful goal from Ronaldinho but had to settle for a draw after Diego restored parity on 34 minutes. Simone Pepe and Amauri couldn't convert their respective spot-kicks, propelling Milan to a win in their first game of the evening.
Juventus started the match the brighter of the two sides and could have gone 1-0 up as early as the fifth minute when a Diego freekick was headed over the crossbar by Amauri. The Italy international striker had another chance to score just three minutes later but this time too he couldn't keep his header on target.
Juve continued to ask questions of the Milan backline as in the 12th minute Diego's shot from inside the Rossoneri penalty area was saved brilliantly by goalkeeper Marco Amelia.
The Milan custodian was again present to deny Juve two minutes later when he kept out Davide Lanzafame. The Italy international made yet another save on 16 minutes, this time keeping Diego out.
Much against the run of play Milan took the lead on 21 minutes when a Rossoneri attacking move saw the ball spread wide to Ronaldinho on the left, who ran a few yards with the ball and curled it into the net.
However, the Turin-based side could have restored parity just two minutes later when Amauri found himself in an one-on-one situation with Amelica thanks to a defensive error but failed to get past Amelia.
The former Roma goalkeeper again saved Milan in the 25th minute when he comfortably claimed Diego's header from a Marco Motta cross from the right.
But the 28-year-old was eventually beaten in the 34th minute when a brilliant Juventus build-up saw Lanzafame pass the ball to Diego inside the Rossoneri penalty area and the Brazilian slotted the ball home.
It finished 1-1 between Milan and Juventus at the end of the 45 minutes after which the penalty shootout was called for. Massimiliano Allegri's side won the shootout 4-2 as Simone Pepe and Amauri couldn't convert their spot-kicks.
The third match in the Trofeo TIM Cup between city-rivals Milan and Inter will start shortly.