As the Saints prepare to celebrate 50 years since their lone flag, a new documentary details the years of frustration the club has endured, including the four grand final losses and a draw since Barry Breen's wobbly punt secured a one-point win in 1966.

This includes the agonising defeat to the Cats in 2009, and the draw and subsequent loss to Collingwood a year later.

In the documentary, to air on Fox Footy on Tuesday night, Koschitzke was asked whether he was haunted by those results.

"I don't think it's too strong [a word] because you certainly think about it a lot. You wonder if your life would be different," he said. "It's a great question – I don't know what is the answer."

In the moments after those defeats, Koschitzke says he had wished he had not had the chance to play on the biggest day of the AFL calendar.

"To go through that hurt, especially after losing the second one, I would rather have not made the grand final. But now, as years go on, I am absolutely grateful we had the chance but it doesn't ease the pain," he said.

"I think if we executed right, the Geelong game goes down as a St Kilda premiership. That hurts for the fact we were clearly the best side for the whole year. I don't think anybody can dispute that, winning 19 in a row, and finishing on top. I think we lost three games for the year. If you look at a dominant year, that's the one that got away.

"When I think about the Geelong grand final, I think about missed opportunities in front of goal. I remember just dominating the play and we kicked 4.5 [in the second term]. Four-five sometimes might be rushed behinds or hard shots or whatever but you'll find the five points were gettable shots from the top of the square."

He said this poor kicking had "sapped us" by the main break but the Saints continued to fight, with the game turning on Matthew Scarlett's now-famous toe poke to Gary Ablett in the middle of the ground.

The documentary also discusses the lost 1997 grand final to Adelaide and the sacking of coach Stan Alves a year later.

Former St Kilda president Andrew Plympton says club great Trevor Barker had been "ordained" as a future senior coach and his death in 1996 had meant the Saints looked to Tim Watson after Alves' departure. Watson lasted only two seasons, finishing 10th and 16th.

While much has been made of the impact of the round-12 loss to the Hawks in 1999, when the Saints squandered a 63-point lead, Plympton says the inability to hold on to a four-goal lead at half-time against Collingwood the next week was the "killer".

"At the end of the first season, Tim realised, and we all got to realise, that Tim's style of management of people ... perhaps that was Tim's weakness," Plympton said.