Alflaila came from last to first under Jim Crowley to plunder the Group Three Sky Bet And Symphony Group Strensall Stakes at York.
Masekela set a decent pace in the nine-furlong contest and still held every chance with a furlong to race, yet once the former champion jockey found his rhythm, the Owen Burrows-trained son of Dark Angel found another gear.
The 3-1 chance became the first three-year-old to win the contest since 2009, having two-and-a-quarter-lengths to spare over Finest Sound, who stuck on well under Silvestre de Sousa.
Mighty Ulysses, sent off the even-money favourite, proved disappointing, briefly flattering until his run petered out with a furlong to race.
"He can set your heart racing a bit because he steps slow, but that suits him and coming up in trip now I felt he hit the line strong," said Burrows.
"He galloped right around the corner and I think another furlong wouldn't go amiss. They got racing and just left him a little flat footed for a second but once he hit top gear he got into his stride and did it well.
"He won first time at Ascot, he just missed the break in the Jersey and looking back now, he was never going to be competitive then. He ran well at Newmarket, he's progressing nicely.
"This is a Bahrain win and you're but that's in November, he's in on Arc weekend in the Prix Dollar on the Saturday but Anmaat is in that as well, we'll see. "
