The Lancashire sides, two divisions apart in the English pyramid, will battle for a spot in the second round, with an away tie against Rotherham United looming.
After a concerning start to the National League season by their own expectations, Stockport County appointed Dave Challinor as their new boss, and they headed into his first game in charge - the trip to Bolton - full of optimism for the future.
Ben Whitfield levelled the game on the stroke of half time, and Hatters held on for a surprise draw, forcing Bolton to travel to Edgeley Park.
Challinor's first league game in charge, a home clash against Bromley on Saturday, did not go to plan in the same way, as they looked set to see out a 1-0 win thanks to a Quigley goal, only for the visitors to snatch a point and force a share of the spoils in 90th minute through a Liam Hogan own goal.
Before they focus on climbing the league, Stockport will now look to again surprise the League One outfit and go one better to reach the second round of the FA Cup with what would be an eye-catching win.
The visitors arrive on the back of a much-needed league win, having previously struggled for form.
Ian Evatt's men headed into the first-round clash with Stockport on the back of a five-game winless run in the league, seeing them drop away from the playoff places, and they rebounded from the disappointment of the draw with a victory on Friday.
Having now regained confidence thanks to that win, the Trotters will look to avoid a cup upset on Wednesday and get over the line when they travel to the fifth-tier outfit.
Stockport attracted attention with the signing of Bolton captain Antoni Sarcevic in late October, and, after missing the trip to the Macron Stadium through injury, the midfielder will now be fit to feature against his former club in the replay.
Scott Quigley and Paddy Madden offer plenty of threat going forward, having hit three and four goals respectively so far this season, with the former scoring in the 2-2 draw.
Bolton deployed a full-strength starting XI for the home clash against Stockport, and Evatt will keep the same approach for the replay.
Experienced forward Eoin Doyle should continue to lead the line after finding the net in that game, although Amadou Bakayoko will also hope to feature after hitting the first goal in Friday's win over Crewe.
Meanwhile, winger Elias Kachunga also scored in the 2-2 draw and Oladapo Afolayan has made the other flank his own.
Stockport County possible starting lineup:
Ross; Minihan, Hogan, Palmer; Crankshaw, Rooney, Sarcevic, Croasdale, Whitfield; Madden, Quigley
Bolton Wanderers possible starting lineup:
Dixon; Isgrove, Santos, Baptiste, John; Lee, Williams, Sheehan; Kachunga, Doyle, Afolayan
We say: Stockport County 1-2 Bolton Wanderers
Despite the difference in level, we certainly do not see this as a straightforward victory for the visitors.
Stockport will give everything to eke out a result on home turf, but we ultimately see them falling just short to the quality that Bolton possess.
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