Calzaghi and Robbie Colgan © Photo Healy Racing
The Kevin Coleman trained Calzaghi stayed on best inside the final furlong to land Division l of the Yellow Furze Handicap at Navan.
Having missed the break on his handicap debut at Tipperary last time, the Raven's Pass gelding caught the eye with his strong late run to finish fifth.
Again, slowly away here, Robbie Colgan soon had the 7/1 chance tacked on at the rear of the field.
Still nearer last than first with over two furlongs to race, Calzaghi began to weave his way through the runners as Special Angel kicked for home under Robert Whearty.
Moving second over 100 yards out, the eventual winner powered up the stiff hill to overhaul the leader, going away to score by two-and-a-quarter lengths.
Robbie Colgan said: "I didn't know much about him. I saw him running the last day, and he ran really well and finished it off good.
"He was a little slow away again, but finished out really well.
"You'd hope so (have a future at that trip) - they went hard and he finished up the hill really well.
"Kevin is brilliant, he said he hoped he would have a chance."
Additional reporting by Michael Graham.