Frankie Dettori's mount Willing Foe pipped Royal Diamond on the line to win the showpiece Ebor race at York.
Willing Foe (12-1) battled hard to overhaul 16-1 chance Royal Diamond on the run-in, with Number Theory third and 7-2 favourite Motivado fourth.
"It's taken 25 years [to win the Ebor] but my day has come," said Dettori.
"He's a great horse, he showed tremendous determination at the end. Quietly, I thought I had a chance but it is the Ebor."
Crackentorp made all the running from Royal Diamond before the field fanned out to contest the finish inside the final four furlongs of the 1m 6f trip.
Luke Morris and Motivado briefly threatened to surge from a long way back but Royal Diamond remained firm as Crackentorp faltered before Willing Foe got up to mount his challenge.
A stewards' inquiry followed but the places were unaffected.
"I knew I would keep the race (after the stewards' inquiry)," added Dettori. "I did drift over a bit, but I beat the other horse fair and square. I might get a small holiday(suspension).
"This is one of the most important handicaps of the season and now I've conquered it.
"I didn't have many boxes to tick, but this was one of them.
"I know it's only a handicap, but it's a very prestigious race and it's always a great crowd here.
"It's a funny old game, 24 hours ago I was sat in a car with the doctor (after a fall)."
Winning trainer Saeed bin Suroor said: "The options are open for him. We'll have a look at everything, but he is a possible for the Melbourne Cup.
"We've got a few in it, but I think the trip would be perfect for him."
Ebor handicap results:
1 Willing Foe (L Dettori) 12-1
2 Royal Diamond (N G McCullagh) 16-1
3 Number Theory (R Kennemore) 16-1