[3] In 2006 D'Agostino played in the Pacific Coast Soccer League for Whitecaps FC Reserves with whom he won the championship.

Blackpool manager, Simon Grayson said of the move, "This is a great opportunity for the lad to go and play some first team matches and we will be monitoring his progress closely.

[9] Following three substitute appearances, D'Agostino made his full debut for the club on 29 December in a 1–0 away defeat to Tranmere Rovers.

He received praise from the club's manager, Keith Downing, who said he had a "terrific home debut",[13] D'Agostino won the "Man of the Match" award.

The club's fans nicknamed him "Daggers" and his loan spell was due to end following the 1–0 home defeat to Millwall on 29 January.

Keith Downing said of the deal, "Hopefully they (Blackpool) are pleased with the progress Michael has made with us as we are helping him develop as a player as well."

[19] On 20 February 2009, after a short trial, D'Agostino joined League One club Hereford United on an initial one-month contract.