2004 started excellently, with Dal Santo playing in St Kilda's 2004 Wizard Home Loans Cup winning side.

[3] Dal Santo had an excellent Premiership season, playing every match, averaging over 18 disposals a game, and kicking 11 goals for the year.

Former Essendon Football Club coach Kevin Sheedy, during the 2005 season, likened Dal Santo to triple-Brownlow Medallist Ian Stewart for his exceptional skill and courage.

In that same year, former Hawthorn champion Gary Ayres said this of Dal Santo in an interview: "He's got a high skill level on both sides of his body.

He doesn't seem to get too flustered or rushes it, and that's a pretty special quality to be able to have when you play elite football because a lot of players can get the ball but do they make the right decision?"

Early in the 2006 season St Kilda lost star midfielder Lenny Hayes to a knee ligament problem and the captain, Luke Ball, was also struggling with injury.

In Hayes absence Dal Santo began to cop a heavy tag from opposition teams each week and this lessened his impact on the game.

The temporary demotion spurred Dal Santo on to a good finish to the season – picking up 530 possessions (including 335 kicks), 12 goals and 75 tackles.

Although his form was down on that of previous seasons, he picked up Brownlow Medal votes in two games and also played a major part in St Kilda's semifinal victory over Collingwood, with 32 possessions, five tackles and one goal.

[7] St Kilda dominance over the other league teams for the year was consolidated by a 6 point win in Round 14 over Geelong at Marvel Stadium, in front of the largest crowd ever for an AFL game at the venue in history of 54,444.

Dal Santo played in the grand final against season nemesis Geelong, in which St Kilda were initially listed as defeated by 12 points, which became the subject of an ongoing investigation.

He also came a close second in St Kilda's best and fairest Trevor Barker award, which recognised his consistency and leadership in the absence of Lenny Hayes.

In 2012 the Saints appointed a new coach in Scott Watters, and had a competitive season that finished in an underwhelming 9th position, not getting to play in the Finals Series for the first time since 2007.

At the end of the season, Dal Santo was regularly questioned about his playing future, consistently stating he wanted to do what was best for St Kilda Football Club.