Had he passed the ball into the net, a task that seemed so bloody simple, it would have been the golden goal in the game (when this actually existed), that would have taken us through to an FA Cup Final against Chelsea in 2000.
To many people's surprise, perhaps, he spent the longest period at one club of his strangely iconic football career with the mighty Whitemen.
His signing in the summer of 1997 by Colin Todd was seen as something of a coup, as the then 28 year-old greasy lover was in his prime, with a proven Premier League goalscoring pedigree in his locker.
Young Dean started his footballing journey as an apprentice at Watford, alongside his twin brother and later his fellow Wanderers teammate (well, squadmate lets say), David.
While David progressed through the ranks to become a Hornets legend, amassing 258 league appearances at Centre-Back in the famous yellow shirt over ten long years, Dean struggled to make an impact at Vicarage Road.
Loan spells down the league at Carlisle United, Port Vale, Swansea City and finally Brentford over two seasons yielded a slim total of five league goals.
His spell at the latter was impressive enough, however, for ex-Spurs legend Steve Perryman to take a punt on the young lothario-to-be and turn his move into a permanent one.
Holdsworth hit the ground running and his spell at Griffin Park over three fruitful seasons set him on the road to usurping Coronation Street favourite 'Reg' as the most famous Holdsworth in the world.
A ratio of just under one in two per game in his three seasons yielded 53 goals in 110 appearances as Brentford yo-yo'd between the old 2nd and 3rd divisions with the only constant being Deano's predatory instinct for banging in the goals.
This made the-then highly thought of manager of Wimbledon, Joe Kinnear, sit up and take notice as he sought to bring the young English marksman to Selhurst Park to play his football in the bright lights of the Premiership.
Dean made his move to the Crazy Gang for a hefty £650,000 fee in the Summer of 1992.
His 5 years spent with the original Dons were highly influential in the history and success story of this motley crew of waifs and strays that still beguiles the nation to this day.
Theirs was as pure of an example of true underdogs overcoming prejudice and adversity to achieve (comparative) glory in amongst the elite of the game.
In four seasons under Joe 'Facking' Kinnear's shrewd stewardship he scored a mightily impressive 58 goals in 169 1st division (as it was known) and then Premiership appearances.
This even led to international recognition, of a kind, in the form of an England 'B' cap, Holdsworth scoring the opening goal in a 4-2 win over Northern Ireland 'B' at Hillsborough on 10th May 1994.
There was clamour amongst certain sections of the media for his inclusion in the full England set up, such was his enviable goal record.
However, plying his trade at such an unfashionable club left him overlooked by first Graham Taylor and later Glenn Hoddle, despite other strikers of similar ability getting their opportunities.
During his time at Selhurst Park, bizarro club chairman Sam Hammam promised to buy Holdsworth a Ferrari (despite the fact he probably owned 3 already) and even a camel (don't ask) if he managed to score 20 league goals in a season.
Holdsworth never quite managed to reach that target.
He hit 17 league and seven cup goals in the 93-94 season, including a memorable hat-trick against Oldham Athletic in April 1994.
He was less prolific in the 94-95 season, though Wimbledon still finished in 9th place.
He resumed his goal trail by netting 16 goals in 95-96 to become the club's joint-top scorer, along with strike partner and notorious lanky beanpole Efan Ekoku.
He hit nine goals in the 96-97 season before Todd made his unexpected swoop for his services.
The fee was considered a huge outlay for a club like ours and indeed broke the club record transfer fee.
The start of his Bolton career was inauspicious as a combination of poor form and niggling injuries meant he only mustered three paltry goals in seventeen Premiership starts as the Wanderers were cruelly sent down on the final day with defeat at a Chelsea side who Deano had downed with a 72nd minute winner at the Reebok earlier in the season, in his most memorable moment in a White shirt that season.
The following two seasons, spent chasing a return to the promised land but ending with play-off heartbreak, yielded an impressive haul of 26 league goals in 50 starts as he led the line in a talented team who were broken up each Summer as the vultures circled.
Our third tilt at promotion under Big Sam's canny leadership saw Deano rotate with young upstart Michael Ricketts for the lone striker's role, Holdsworth often tiring defenders out with his tireless running and physical play to leave Ricketts the role of substitute destroyer late in games, taking advantage of the fatigued opposition.
15 goals in 29 starts in all competitions included a hat-trick in the 5-1 league cup rout of Scunthorpe United, which put him amongst a small bracket of Wanderers players who have taken the ball home with them since the turn of the Millennium.
Deano's return to the top league was mainly spent as an impact substitute but did include the hilarious late winner which sent us briefly top of the league in late August 2001 as Sander Westerveld fumbled his late ambitious pea roller into his net to much mirth in the stands as Liverpool were defeated 2-1.
One further goal vs Spurs was the sum total of ten appearances that season as Wanderers completed their mission to survive.
His Wanderers journey ended the following December as a loan spell which returned six goalless games for Coventry somehow persuaded them to sign him.
He had fallen way down the pecking order at The Reebok with French World Cup Winner Youri Djorkaeff and unpredictable Danish striker Henrik Pedersen prominent in Allardyce's thoughts.
Now 34, Holdsworth began a nomadic journey down into the depths of the lower leagues and then non-league, taking in spells at Rushden & Diamonds, Wimbledon again and a goal laiden season at Havant and Waterlooville which prompted an unlikely sojourn at Derby County.
Weymouth, Heybridge Swifts, Cambridge United, Newport County and finally Redbridge all got to taste the unique experience of Deano's indomitable character leading their forward line before he finally retired aged 39, when offered the managers role at Redbridge after a short spell as player/manager.
Three successful years at Newport County that included their romp to the Conference South title saw Holdsworth's stock rise and Aldershot gave him a chance in league football management.
Despite a decent start he was dismissed after just after two years in charge in February 2013.
An ill-fated five month period in charge of Chelmsford City ended in August 2013.
His hold up play, impressive heading in front of goal and instinctive finishing made him the archetypal English centre forward and his penchant for a page three model further endeared him to the tabloids and the 'man in the street'.
Holdsworth was a divisive figure amongst Bolton fans but he must be remembered for his contribution in those vital years pressing to return to the Premier League and for laying the foundations that led to us being able to marvel at the legends that went onto wear the famous White shirt under Big Sam.
That miss though...