Then there was the occasion when football's first lady went to London to defend the club against the allegation that it had attempted to poach a rival manager. Before the hearing, one newspaper suggested that rather than argue her case she was preparing to "do a Sharon Stone" by re-enacting the notorious leg-crossing scene from Basic Instinct, presumably in an attempt to bamboozle the geriatric blazer-brigade sitting in judgment before her.
There was also her first away match at Watford, when one hapless steward tried to direct her to the directors' wives' box rather than that reserved for the game's real movers and shakers. And then, of course, there was the celebrated goal scorer who considered it his rightful place to cast a leering eye over his new boss's blouse and praise the way it showed off her breasts.
But to gauge how times have changed, it is necessary to scroll forward a dozen or so years. This time, the scene is Lancaster House and inside the gilded Hanoverian mansion, the Birmingham City boss is sitting down to a charity dinner of roast fillet of Cornish sea bass with 150 fellow high-profile women. The event is being hosted by Prime Minister Gordon Brown's wife Sarah, the guest of honour one Carla Bruni-Sarkozy, the dazzling new wife of the President of France.
For Ms Brady, now with a string of directorships including Mothercare and Channel 4, and a mantelpiece groaning under the weight of Businesswoman of the Year awards, those early days of intrusive, insulting questions, of being the unknown women striving to be taken seriously in the devoutly masculine world of football, must have seemed to belong to a different era. Yet this week, having charted a meteoric course from lieutenant to the pornography baron David Sullivan, to become the youngest managing director of a publicly listed company, star of The Apprentice, and celebrity patron of dozens of good causes, Ms Brady was again facing uncomfortable questioning. This time, rather than fending off Fleet Street's finest, it was the turn of officers from the City of London police to do the probing after she and Mr Sullivan, a fellow director at the club, were arrested as part of a long-running investigation into football corruption.
Their questioning on suspicion of conspiracy to defraud and false accounting in relation to the £300,000 transfer of the Sengalese star Aliou Cisse and another African player came a month after police raided the club's offices, seizing computer files and documents.
According to Birmingham City the two, who have not been charged, voluntarily attended the appointment with detectives. Mr Sullivan's Essex mansion, the centre of his publishing operations, was also searched.
Yesterday, both were said to be "enraged" by suggestions that they had been involved in taking so-called bungs and vehemently deny any allegations of wrongdoing.
In a statement, the club insisted the inquiry was concerned simply with the possible non-payment of PAYE and National Insurance contributions.
But still the arrests have sent shockwaves through the world of football. Trading in Birmingham City shares was temporarily suspended and fans were left wondering what was in store for their club as it battles to keep its hopes of Premiership football alive this season.
The arrival of Ms Brady at St Andrews in 1993 at the tender age of 23, was always going to prove an astute PR move for Mr Sullivan, owner of the Daily and Sunday Sport newspapers. For theirs was a unique if unlikely relationship that has long held a fascination with the media.
Mr Sullivan is the diminutive street-wise businessman, who brought a young Mary Millington to eager British audiences in the 1970s and made a fortune out of his string of Private Shops. She, by contrast, was the glamorous, privately educated girl from north London, who always insisted that her boss's pornographic activities were just another area of business.
Yet despite the apparent differences, the two were united by a driving ambition and relentless refusal to suffer fools gladly. Ms Brady grew up amid affluent surroundings. Her father, a self-made millionaire, drove a Rolls-Royce and the family holidayed not at Butlins, like her local friends, but in Barbados. She inherited a sense of style and attention to detail from her Italian-born mother who, she told Kirsty Young on Desert Island Discs recently, wore a new evening gown every Saturday night, even dying her cigarettes a colour to match her dress.
As well as being a stylish household, it was also an entrepreneurial one. Ms Brady and her brother used to dream up money-making exploits from the age of six or seven, she recently recalled, offering services in everything from car washing to massage, something which didn't always go down well with her concerned parents.
After completing her studies at various boarding schools, including a stint at a Hertfordshire convent, she felt university would only delay her ascent into the commercial world and she joined advertising agency Saatchi & Saatchi aged 18. It was a decision she never regretted and by the time most of her peers were dragging themselves out of bed to sit their finals, she was already working hard at a second sales job at the radio station LBC.
Here she first encountered Mr Sullivan. Tasked with the unenviable job of flogging advertising for the pre-dawn Asian Hour, Brady approached the tycoon touting for business only to be turned down flat. He insisted that radio advertising didn't work. She said it did and hung around outside his mansion in an attempt to prove to him face to face that it could.
Seriously overstepping her pay grade, she offered him guaranteed sales rises or his money back. Mr Sullivan, who knows a good offer when he sees one, was soon shelling out £2m on radio advertising.
It was only a matter of time before he decided he needed this determined young woman working for him and once inside the Sullivan stable it was Ms Brady who spotted the £700,000 opportunity posed by a fire-sale advert in the Financial Times for Birmingham City football club.
At that stage, the Blues were in receivership and languishing in the second division. The following season the club was relegated again and Ms Brady was facing a mounting criticism from fans for supposedly attempting to involve herself with the football rather than the business.
The controversial hiring of the Southend United manager Barry Fry failed to stem the decline. But, by 1996, things were on the up. The club posted its first profit and a year later it was floated. Ms Brady pioneered a myriad of revenue-generating projects, everything from credit card deals to a funeral company. She also set out to make the club more family friendly, offering cut-price deals for children. Eventually, Birmingham delighted its returning army of fans – as well as its shareholders – by securing a lucrative Premiership place in 2002.
Ms Brady's private life had also mirrored the club's success, despite the punishing long hours she has kept and which required her to live for several years in a hotel. Sources close to the club recall how she was always on hand to mop up after the daily scrapes into which every group of footballers seems drawn, offering a reassuring word of advice and an uncanny ability to keep some of the more salacious aspects of her players' lives out of the newspapers. Along the way, she says she developed "balls of steel". Others saw an up-front, no-nonsense operator of the what-you-see-is-what-you-get variety.
In 1995, after enduring a courtship stalked by photographers hiding behind bushes and upsetting at least one Birmingham grandee, she married the Canadian footballer Paul Peschisolido, not that she allowed sentiment to get in the way of business, having since sold her husband twice to help raise cash for the club.
The couple have two children and she has continued to juggle a six-day week with the rigours of child care, having attended one board meeting just three days after giving birth.
But perhaps her greatest drama came in 2006 when doctors discovered a potentially life-threatening cerebral aneurysm during a routine scan. The only course of action was to operate, so packing her favourite pillow, one she has taken with her since childhood, and despatching an email to the club telling them she would be back at her desk in a couple of weeks, she went into hospital.
Having been given the all clear, she has returned to work with typical gusto, preparing the way for a potential takeover by Hong Kong businessmen and facilitating the arrival of the new manager, Alex McLeish.
With survival in the Premiership now all but assured, the future was once more looking bright. But those that know her believe that the present travails will do little to dent her plans for life outside football, and that she will emerge from the experience both stronger and wiser.
Her world view is neatly summed up in a picture of a golden eagle hanging in pride of place above her desk at the club. It says: "Leaders are like eagles. They don't flock. You find them one at a time."
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