Massiyn landed some hefty bets when opening his account for the in-form Mick Halford in the opening 10-furlong maiden at Roscommon last night.
Sixth behind Saturday's Irish 2,000 Guineas contender Takar on his sole start as a juvenile, the son of Zamindar was supported in to 3/1, having opened up around the 8/1 mark earlier in the day.
Johnny Murtagh held onto his mount for as long as possible, until unleashing him at the furlong pole where he swept past long-time leader Encrypted Message to record an eased-down length success.
Halford doubled up when saddling the tenacious Paddy The Celeb to victory in the featured 12-furlong handicap. The 4/1 favourite held off the challenge of Statesmanship close home.
Murtagh was also in double-winning form, partnering the John Oxx-trained Shamooda to victory in the other 12-furlong handicap.
The race appeared to revolve around Saturday's facile Wexford scorer Time Of My Life, sent off at odds of 2/9, but he could only finish third.