Taylor had tasted play-off defeat with Brentford at the hands of both Crewe and Huddersfield, but when he played for Gillingham against Manchester City at Wembley on 30 May it seemed his day had finally come.
All the significant action in the Second Division play-off final came at the end. One up after 81 minutes, they were on their way to the First Division when Taylor scored their second five minutes later. "I just remember flicking it to Carl Asaba and shouting for him to back-heel it. I took a couple of touches and drilled it past Nicky Weaver."
Taylor has only recently been able to bring himself to watch the video of what happened next. "We only averaged seven or eight thousand at home, but there were 30,000 at Wembley. It was an amazing turn-out and they thought we'd done it. We thought we'd won as well, but we just got penned in our own half and couldn't get out. It was all hands to the pumps and I was the only one left upfield."
Despite their efforts to cling to the prize of promotion, Gillingham conceded a goal to Kevin Horlock in the last minute of normal play and an equaliser to Paul Dickov deep into injury time as City mimicked Manchester United's late, late show in the European Cup final four days earlier. After all that activity, it was, says Taylor "very cagey in extra-time. Nobody looked like scoring".
And so to penalties, with Taylor, the Gills' regular spot-kick taker during the season, a frustrated spectator as their dreams drained away. He was fifth in line, but was never called upon; by that time, Gillingham had missed two, the second of them saved by Weaver from Guy Butters. "It was devastating for the lads who missed, but it's pot luck and you can't blame them."
Gillingham trudged off to the strains of "Blue Moon", as Manchester City celebrated one of the season's great escapes. "We had to get over it, but it was the sort of thing that takes a while to get over," says Taylor.
For him, there is a bitter-sweet twist in the tale, because in November, he joined the club that had broken his heart in May. "I suppose I nearly broke their hearts," he explains. "I believe they were looking at me before the play-off final, but I didn't know about their interest until this season." At which point he became a City player for pounds 1.5m.
Even with their recent stutter, that makes him part of another promotion- seeking side, but he has just one wish for the remainder of the season.
"I'd rather avoid the play-offs this time," he says. "I've never experienced automatic promotion and I'd like to try it."
After that nail-biting failure at the hands of his current team-mates, who could blame him for that preference?