For the vast majority of the second-half, Federico Agliardi's goalkeeping heroics kept the hosts at bay until Emanuele Giaccherini's 90th minute strike appeared to steal victory for Juve.
However, Andrea Raggi headed home a corner in the 95th minute to send the match into extra time.
Once there, a brilliant individual goal by Claudio Marchisio settled the tie in Juventus' favour.
The first half was not one for the purists, with both sides struggling to establish any kind of attacking rhythm.
The most notable moment for the visitors came courtesy of Daniele Vantaggiato, who forced Marco Storari into a diving save from a free-kick 23 minutes in.
Juventus were not faring any better, with Milos Krasic at the heart of what little they created in the opening period.
The Serbian first had a goal correctly chalked off for outside, before teeing up Fabio Quagliarella for a shot that was blocked by Agliardi a few minutes before the break.
Antonio Conte's men continued to create chances in the second half, and Alessandro Del Piero should have done a lot better in the 57th minute, dragging his finish wide when a missed header by Raggi left him one-on-one with the keeper.
The Bianconeri skipper had another chance 10 minutes later from a free kick, but Agliardi was again equal to his effort and smothered the ball low at the far post.
Giaccherini finally broke the visitors' resistance on the stroke of injury time with a goal of some quality.
The substitute burst from midfield, storming past two players before drilling his finish high into the back of the net.
But Just when it seemed like Juventus had stolen a berth in the quarter-finals, Bologna managed an equaliser five minutes into injury time from the unlikeliest of sources.
A corner from the right was headed in emphatically by Raggi to send the tie into an additional 30 minute period.
The home side controlled the first half of extra time, and regained the lead just as the game clock moved into triple digits.
There did not appear to be a lot of space for Marchisio to work with when he was fed near the penalty spot, but the Italy international evaded his marker with a clever shimmy before planting his finish expertly into the bottom corner.
With the win, the Serie A leaders become the first side to seal their place in the Coppa Italia quarter-finals.
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