Since moving into management, however, the 49-year-old has been making up for lost time.
Knocking out Jose Mourinho’s Chelsea in 2015 meant Parkinson’s Bradford City made headlines around the world but that stunning fourth round triumph at Stamford Bridge is far from his only entry into Cup folklore.
In fact, the Bolton Wanderers chief’s CV contains so many fairytales in the world’s oldest knockout Cup that even the most passionate fan of the Brothers Grimm could be enraptured for hours listening to them all.
No wonder, therefore, Parkinson attaches huge significance to a competition that began life in 1871 and tomorrow will pit together two past winners when Sheffield United travel to the Macron Stadium.
“I love the FA Cup,” he said when speaking to The Yorkshire Post ahead of tomorrow’s eagerly-anticipated tie between two of League One’s top three sides.
“It has a little bit of everything and allows everyone to dream. The Cup is the only competition where, as we did one year at Colchester, you can play Leamington and then Chelsea at Stamford Bridge in the same season.”
Parkinson’s first taste of management in the Cup came at Layer Road. He was 35-years-old when handed the reins in February, 2003, with the specific target of preventing the U’s being relegated to the basement division.
Mission accomplished, he quickly set about the task of turning Colchester into a club who, by the time he left for Hull City in the summer of 2006, was in the Championship and had three stirring FA Cup runs in as many years to their name.
Two appearances in the fifth round sandwiched a run to the fourth round and there were plenty of highlights along the way, including a club record 9-1 win over Leamington.
Then there was his first of two Cup meetings with Mourinho’s Chelsea.
“I always remember that draw and seeing just what it meant to people behind the scenes at the club,” he recalls about a run in 2005-06 that included beating Sheffield United, then en route to the Premier League under Neil Warnock, a couple of rounds before landing that trip to the Bridge.
“They knew the financial aspect and what a boost it would be. Our budget was probably the lowest in the division at the time so drawing Chelsea away was massive because it meant a 42,000 sell-out crowd.
“I couldn’t tell you the exact figures but I bet the money we earned wasn’t far off being enough to pay the wage bill for the entire season.
“As vital as that was, though, I think the staff were more pleased at how the draw had put Colchester United back in the spotlight.”
Nine years on, Parkinson would return to Stamford Bridge and inspire ‘that’ remarkable 4-2 win for Bradford. What few outside Colchester realise, however, is just how close he had been to pulling off an upset first time around.
“We took the lead and then hit the post when a goal would have made it 2-0,” he recalls. “If that had gone in, who knows what would have happened?”
Mourinho’s response was to bring Frank Lampard, Joe Cole and Hernan Crespo off the bench and the Blues went on to triumph 3-1. The Portuguese, of course, tried something similar against Parkinson’s Bradford but, this time, Eden Hazard, Cesc Fabergas and Willian were unable to rescue the situation. It is a day that neither Parkinson nor any of those 6,000 travelling fans from Yorkshire will ever forget.
“One of the big memories I have is the drive from the hotel to the ground,” he said. “Every single pub we drove past was rammed with Bradford fans.
“All you could see was claret and amber, and supporters waving at the coach. As a staff, we still talk about it today. It was a wonderful sight and I could sense the inspiration the lads were taking from it. The key was channeling that once we got to Stamford Bridge.”
City, of course, did just that. Despite falling 2-0 behind to goals from Gary Cahill and Ramires, the League One side had halved the deficit by half-time through Jon Stead’s strike.
What followed in the second half was truly remarkable as the Bantams pulled off arguably the biggest Cup shock of all time against a Chelsea side who not only led the Premier League by five points but had won all 14 previous home games that season.
Goals from Filipe Morais, Andrew Halliday and Mark Yeates meant a side whose starting XI cost £200m had been humbled by one put together for just £7,500. Even that modest sum had been spent on James Hanson before Parkinson’s arrival at Valley Parade.
“We were 2-0 down but not playing too badly,” he recalls. “I wasn’t too concerned about what might happen, not worried that it might go terribly wrong. I just wanted to try and give the lads some belief.
“Then came the goal by Steady, who had an incredible game that day, and suddenly it all changed. We took the game to Chelsea in the second half.
“Jose Mourinho was in the technical area and I could sense he was thinking: ‘This is going to be hard because we can’t just turn it on’. Steve Parkin came up to me after the equaliser went in and said: ‘We are going to win this’. He was so certain.
“Afterwards, Jose came into our dressing room. It was clear he was hurting from the look on his face. But he was brilliant. He shook all the lads’ hands and praised them for how they had played.
“A lot of teams came to Chelsea back then just to defend but we hadn’t and Jose said he was impressed by that – and that we deserved to win. I know what it is like to lose a big game but he was brilliant with us.”
Another Premier League side in Sunderland was dispatched in the next round before City’s fairytale run was ended by Reading after a replay in the quarter-finals.
Missing out on a third trip to Wembley in as many years under Parkinson was a blow and one that hurt, not least because of what he still sees as the FA’s intransigence.
“Making us play the replay on a Monday night was wrong,” he said. “Reading had rested all 11 players two days earlier but we didn’t have that luxury and lost 3-0.”
Parkinson may have been upset with the FA in 2015 but he was pleased with the governing body’s recent decision to reject calls for a revamp that would have seen ties played in midweek and all replays scrapped.
“I was really pleased when the FA announced the Cup was staying as it is,” he added. “Heritage is important and this is the oldest Cup in the world. Fans love it and we have to nurture it.
“The FA must do everything to protect the Cup, it is recognised all over the world. We found that out at Bradford after beating Chelsea.”