His team trailed by 10 points in the fourth quarter in 2004, and by seven points in 2008. He won both of those games.
Roethlisberger's return to Dallas in 2012 saw his team up by seven in the fourth, only to watch the lead disappear.
Similarly to the Steelers other two overtime games - a loss at Denver in the playoffs and a win vs. Kansas City this year - a big play ended it. Roethlisberger threw an interception to Brandon Carr, who returned it to Pittsburgh's 1-yard line, setting up a chip-shot field goal for the win.
Poor tackling highlighted perhaps the Steelers' worst defensive performance in the last few weeks, but that is at least explainable due to the fact the Steelers had the very bottom of their secondary depth chart covering the high-production receivers of the Dallas Cowboys.
There is no explanation, though, for the execution and decision-making of Steelers receiver Antonio Brown.
His fumble on a punt return set up Dallas' game-tying touchdown, and a decision to not catch a punt pushed the Steelers 19 yards back with under three minutes to play in a tie game.
Brown's fumble came at 10:03 of the fourth quarter, right after the Steelers forced a punt, holding onto a 24-17 lead. The Cowboys took it as a reason to hang another long drive on the struggling Steelers defense. After holding on first and second down at the goal line, DeMarco Murray scored on a zone run, cutting back to the left.
It was another example of the Cowboys' physical dominance over the Steelers in this game. The Cowboys, though, could not execute when it mattered.
Brown chose to not field the punt, letting it roll 19 yards behind him, setting up the Steelers at their own 20. After two sacks on Roethlisberger, Brown chose to run out of bounds on a third-and-long, stopping the clock, letting the Cowboys keep their two timeouts.
The Steelers defense was able to get another stop, forcing a punt. The Steelers knelt it out to end the half.
Fortunately, Brown managed to not damage the team on the coin toss. The Steelers called tails and chose to take the ball. Roethlisberger's interception sealed it.
The Steelers fall to 7-7, and while they still have playoff life, they're playing the worst football of the last three seasons, and will struggle to beat anyone, let alone division rival Cincinnati.
Lose that game, and the Steelers will play their first meaningless Week 17 game since 2006. Win, and it's a Week 17 playoff game against Cleveland.