It was the era that birthed some of St Kilda’s most beloved champions.

Names like Riewoldt, Hayes, Milne, Gehrig, Hamill, Koschitzke, Montagna, Dal Santo, Hudghton, Goddard, Ball, Harvey, Blake and Fisher were held in high regard by the invigorated fans, who could sense they were on the cusp of greatness.

But once again, it never came.

Hailing one of the strongest sides since the ’66 Premiership throughout the mid-2000s, the Saints made several tilts at their second Premiership, but fell agonisingly short of a Grand Final appearance every time.

The Saints’ resurgence seemed like wishful thinking at the start of the decade, with a disastrous 2000 Season – which included 10 consecutive losses to open the new millennium – marking yet another wooden spoon.

St Kilda moved to Docklands Stadium that season as stadium football became the precedent, notching up the just two wins for the year at their new home.

Things began to look up following the club’s ground-breaking trade period at the end of the year, with Aaron Hamill, Fraser Gehrig and Stephen Lawrence bolstering the ranks.

Top-two draft picks Nick Riewoldt and Justin Koschitzke were also brought in to mark the dawn of a new era.

Adding to the excitement was the appointment of Malcolm Blight as senior coach, with the North Melbourne great responsible for coaching Adelaide to September glory over the Saints in 1997.

Unfortunately, the same success was nowhere near close to being replicated at St Kilda.

The Saints languished down the bottom of the ladder with a lacklustre four wins, while the relationship between Blight and the players was stretched to its limits.

Blight forced the playing group to sit in the middle of Colonial Stadium twice after humiliating defeats, receiving widespread media attention and culminating in his sacking midway through the season.

With Grant Thomas stepping in as senior coach, change was on the horizon.

Hamill and Gehrig were huge instigators in the club’s turnaround over the next few years, continually driving the lowly club to reverse its external perception.

Meanwhile, the likes of Riewoldt, Koschitzke and top draft picks Goddard and Ball began to build as elite players.

Reacquainted with their classic tri-colour strip in 2002 and adopting a rotating captaincy policy the following year, the Saints began their gradual evolution from a bottom-tier club to a powerhouse of the competition.

Even with retirements of Stewart Loewe and Nathan Burke, the Saints forced their Premiership window open after a stunning 2004 Season, which featured a then-record of 10 consecutive wins.

2004 was simply a slice of St Kilda magic.

It was the year the Riewoldt truly broke onto the scene and took the next steps into becoming a legend of the game. 

‘Roo’ finished in the top-10 of Coleman and Brownlow Medal, took out his second Trevor Barker Award and reeled in a league-high 256 marks – his courageous grab running back with the flight against Sydney going down as one of the greatest marks of all-time.

Riewoldt would go on to win a record six Trevor Barker Awards, overtake Danny Frawley as the club’s longest serving captain (11 seasons), become the fifth Saint to play 300 games, earn five All Australian nominations and take the most marks in the competition’s history.

Troy Schwarze also wrote himself into St Kilda folklore in 2004 after his last-gasp goal from 60m out saw the Saints knock off triple-Premiership side, Brisbane.

A Coleman-winning season from Fraser Gehrig played a pivotal hand in guiding the Saints to September, with the preliminary final against Port Adelaide resulting in the cult hero’s 100^th goal for the year.

But even with all the chips in place, the Saints would fall short in the penultimate battle, going down by a goal against eventual premiers, Port Adelaide.

The customary ground invasion following Gehrig’s milestone goal is still said to have been the moment which killed the Saints’ momentum.

It was close to an exact repeat in 2005.

Gehrig took out the Coleman, St Kilda finished in the top-four and were again knocked out of the finals race by Sydney, who would go on to claim an historic Grand Final triumph over West Coast.

With a near-identical set of circumstances occurring in 2006, Grant Thomas was shown the door.

With Ross Lyon coming into the fold as senior coach and Riewoldt fully handed the reins as captain in 2008, the Saints continued to impress their dominance during the home and away season.

A top-four finish after a stunning 108-point victory over Essendon in the final round – which catapulted the Saints from seventh to fourth – gave the club a coveted double chance.

But although a different year, it yielded the all-too-familiar result as Hawthorn ousted the Saints and went on to win the flag.

2008 was also remembered for the legendary Robert Harvey, who retired as the Saint with an astounding 383 games under his belt, a club record.

Even with the legend’s time at an end, the red, white and black would piece together its best season to date in 2009.

The Saints won 19-straight games to take out their third minor Premiership, finishing clear on top by two games.

The pulsating clash between the similarly undefeated Geelong, coined as ‘The Battle of the Unbeaten’, went down as one of the club’s most enthralling matches, which was played in front of a record crowd of 54,444 at Docklands Stadium.

With the two unbeaten juggernauts level with just over a minute on the clock, St Kilda ruckman Michael Gardiner – rising like a colossus – reeled in an unbelievable pack mark to put the Saints up and carry on their incredible winning streak.

The Saints stormed home to the tune of a roaring St Kilda fanbase; the wild frenzy and excitement never dissipating as the club reached the 2009 Grand Final.

But in a cruel twist of fate, the Cats would go on to have the last laugh.

Much like Barry Breen’s famous point in 1966, football is built upon small moments which go on to become immortalised in history.

Unfortunately, those intrinsic moments which turn the tides of games fell in favour of Geelong this time around.

Matthew Scarlett’s toe-poke and Paul Chapman’s sealer in the final minutes of the 2009 Grand Final burned into the minds of all St Kilda fans, who struggled to comprehend how their perfect season had ended in heartbreak, again.

It wouldn’t be the last Grand Final berth from the red, white and black. 

But even with all the agony, heart-wrenching sorrow and longstanding suffering across the club’s history, few rivalled the pain that was to come in 2010.