Eoin Doyle had taken the game to penalties with an injury-time equaliser to Alex Samizadeh’s first half strike for the Trotters, but home goalkeeper Will Jaaskelainen saved from Doyle, Liam Grimshaw and Dylan Davidson to put David Lee’s side into the next round at Leyland's Lancashire FA County Ground.
It was a game North End had dominated, Doyle’s effort their 20th shot on target, with Simon Makienok, partnering Doyle and May in a three-pronged attack, setting up the Irishman as early as the second minute, for him to head home, only for the referee to pull it back for a foul by the big Dane.
Academy players Josh Earl and Melle Meulensteen were selected amongst the nine professionals and the former forced a fine save out of Jaaskelainen in the opening exchanges as well, the start of an excellent night for the young Wanderers stopper.
May looked lively on his return to the side; just five days before the year anniversary of his injury, picked up in the closing stages of the Lilywhites’ trip to Fulham in late November 2015 and he also forced a save from the goalkeeper before the game was even five minutes old.
The North End pressure continued as Chris Humphrey showed power and pace to shrug off a defender down the right hand side before drilling a shot just wide of the left hand upright.
Whilst Makienok headed over from close range from Humphrey's whipped cross from the right.
But completely against the run of play the home side opened the scoring on 26 minutes. It was their first shot on target and the goal came from Alex Samizadeh; shooting hard and low into the bottom left corner from 25 yards out.
Right on half-time Jaaskelainen made yet another superb low save, to once again deny Makienok an equaliser as the No.9 headed Humphrey's cross towards goal from ten yards out, but a sprawling and smothering stop from the keeper denied the Dane a goal.
It was almost a comeback to remember for May 11 minutes after the interval when he was played in down a left and channel by Doyle, drove into the box and unleashed a vicious low drive. Jaaskelainen was this time beaten, but the ball flew back off the base of the left hand post to deny the Scot a dream return.
The saves continued from the Bolton custodian in the closing stages. The game became more stretched, with the home side having a couple of half opportunities as well, but it was Josh Earl who was denied when put in by substitute Dylan Davidson three minutes from time, the keeper spreading himself well to save one-on-one with the young PNE winger.
It looked like Bolton would go straight through to the next round until the first of two minutes of added time when Earl this time got down the right hand side and crossed to the edge of the six yard box to where Doyle volleyed home to finally beat Jaaskelainen and take the game straight to penalties.
But it was the Bolton No.1 who came out on top once again, making superb saves from Doyle, Grimshaw and Davidson, with Hyuga Tanner, skipper Sam Lavelle and George Newell all beating Mathew Hudson to give Wanderers a place in the next round.
Bolton Wanderers line-up: Jaaskelainen, Spooner, Honeyball, Barrow, Lavelle (c), Tanner, Willoughby (Green, 61), Earing, Newell, King, Samizadeh. Subs not used: March, Aspinall, Lonsdale.
PNE line-up: Hudson, Meulensteen (Smart, 81), Spurr, Davies, Earl, Huntington (c), Humphrey, Grimshaw, Makienok (Davidson, 62), Doyle, May (Stead, 71). Subs not used: Roberts, O’Neil.
Referee: Mr N Swarbrick