The 22-year-old Corhampton Golf Club ace found the going tough at Augusta, Georgia, as he carded a round that leaves him in a battle to make the halfway cut.
The breathtaking course’s unforgiving nature showed no mercy on the reigning British Amateur champion – as immediately demonstrated as he recorded a triple bogey on the first hole.
A prompt bogey on the par-five second didn’t help his cause, either, but the battling Gregory – who was competing in the sixth group out for the first Major of the 2017 season, failed to let it affect his confidence as he followed that up with four consecutive pars before a bogey at seven saw him make the turn at five over.
A birdie at the par-four 10th, following a wonderful approach shot to within two-and-a-half feet of the pin, gave him and his dedicated supporters present hope of turning around things.
However, a triple bogey at the par-three 12th, after getting into trouble in the bushes above the green, meant he now sat on plus-seven for his round – a kick in the teeth after the joy of sinking a brilliant putt to save par on 11.
To his credit, Gregory, who was playing with former Masters champion Sandy Lyle and Sean O’Hair, who recorded a top-10 finish at Augusta in 2009, responded with a birdie at the par-five 13th to get him back to six under.
But just when it looked like the player, who was clearly enjoying himself, was about to produce a memorable run-in, Augusta’s notoriously tough playing conditions – which were made deadlier by a gusting wind – intervened once more as Gregory recorded two more bogeys (14 and 15) and a double bogey on the last to post an 82.
In the grand scheme of things, it’s a score that was maybe harsh on his overall play, with the Corhampton ace producing plenty of good shots and touches around the green in illustrious company.
By no means did he stand out as an amateur as he rubbed shoulders with the world’s best pros.
At this level, though, small margins can make a massive difference.
But with Gregory having plenty of time between the conclusion of his opening round and tomorrow’s second (5.13pm BST), there’s plenty of time to iron any issues.
And with the majority of the field failing to shoot scores south of par in the challenging conditions all is not lost.
Among those failing to break par included playing partners Lyle (77) and O’Hair (76).