Born in Milan, Lombardy, Daldosso started his professional career at Lombard side Monza. He played 6 games in 2000–01 Serie B. In June 2001 Daldosso, Daniele Degano, Massimo Ganci and Cristian Maggioni were sold to Parma in co-ownership deal for 1 billion each, which made Monza had a player selling revenue of 8 billion lire to boost the financial situation of 2000–01 financial year. Daldosso, Degano, Ganci and Maggioni were also returned to Monza in temporary deal for the 2001–02 Serie C1 season. As a player eligible to both reserve and first team, Daldosso played 7 times that season. Monza relegated again in May 2002 as the last of group A. In June 2002 Daldosso and Ganci were sold back to Monza for an undisclosed fee; co-currently, Degano and Maggioni were signed by Parma outright for undisclosed fee. However both Daldosso and Ganci left Monza in new temporary deal while Maggioni returned to Monza in temporary deal. Daldosso played 19 games for Alessandria in 2002–03 Serie C2. Alessandria finished as the last of group A and Monza seventh of the same group. On 1 July 2003 the loan expired and Daldosso returned to Monza. He played one game less comparing to the last season for Monza, which saw Monza finished eighth of the group. However the club also bankrupted during the season, which the license of the club was transferred to new company "AC Monza Brianza 1912 SpA" from "Calcio Monza SpA". Under new ownership, Daldosso was released.
Daldosso joined Serie D club Voghera in 2004 and played for the team in 2 seasons. In 2006, he was signed by Montichiari, returning to professional football after 2 years in non- professional level. Yet, he played only 18 games for Montichiari. Montichiari relegated back to Serie D in June 2007 after losing the additional "play-out" games.
Daldosso without a club for a season, and in 2008 joined Serie D club Tritium. He won promotion back to Lega Pro Seconda Divisione in 2010, and promoted to 2011–12 Lega Pro Prima Divisione in the next year. He played at least 27 games per season for the Lombard club. He was released again in 2012.
Daldosso represented Serie C2 group A in 2004 Serie C Quadrangular Tournament. In 2007, he received a call-up to Italy Universiade team for a training match. In that match he was a substitute.
