This time was the sweetest of them all.
In the final event of his last Summer Olympics, the reigning champion in the keirin powered around the closing lap to secure one more victory. Hoy's gold medal gave Britain seven out of 10 awarded at the London Velodrome, matching its haul from the Beijing Games.
"Because this is the end, the last Olympics I'm doing, the last Olympic medal I can win, the nature of the whole event," Hoy said, "this one was probably the best."
The 36-year-old Hoy said he'd like to keep competing through the 2014 Commonwealth Games in his native Scotland, but said he was "99.9 per cent sure" that this was his final Olympics.
"This is the perfect end to my Olympic career," he said. "At Sydney, I was just over the moon with a silver medal. If I'd have stopped then, I would have been a happy boy, but to go on to Athens, Beijing and here, I can't put it into words."
Hoy said he was struggling to keep his emotions in check as "God Save the Queen" was played once more, and the British flag was raised over the velodrome infield.
"I was just trying to hold it together. I was thinking, 'Oh, no,'" Hoy said. "It comes out of nowhere. It dawns on you — you realize you won, but it dawns on you that this is it."
Maximilian Levy of Germany settled for the silver medal, and Simon van Velthooven of New Zealand and Teun Mulder of the Netherlands were both awarded bronze when a photo finish could not separate them in a race decided by hundredths of a second.
"He's a legend," Mulder said of the Olympic champion. "He's won six or seven gold medals now, and that's really great. If Chris continues, I don't mind, because he's a great person and a great rider."
Anna Meares of Australia won the women's sprint earlier in the day, beating Britain's Victoria Pendleton in the final, while Laura Trott gave the home nation a win in the women's omnium.
Hoy's six golds broke a tie with rower Steve Redgrave as Britain's top Olympic gold winner and made Hoy the first rider to defend a keirin Olympic title. The Flying Scotsman also matched his teammate and Olympic time trial champion Bradley Wiggins with seven overall medals, also a record for Britain.
He wasted no time waking up the velodrome crowd Tuesday morning.
Put in the first race of the day, Hoy opened the keirin competition by going straight to the front in his first-round match with two laps still to go. Van Velthooven was able to stay with him, but the New Zealand rider didn't stand a chance of overtaking Hoy.
Levy also won his race, followed closely by Mulder — a signal that both were on form.
Hoy used the same tactic as in the first round to win his semifinal race. He went clear of the field and held them off for two full laps to set up his chance for gold.
The motorized derny, which sets the pace for the first 5 1/2 laps, came around to start the final race as a capacity crowd rose to its feet. Levy slotted in right behind, Shane Perkins of Australia was second, and Hoy appeared content to ride around in third.
When the derny exited on the back stretch, the race was on.
Hoy moved up along the outside of Levy and barrelled into the lead on the front stretch, just as he did every round to reach the final. Levy charged back to pass him on the front stretch entering the final lap, and the two were side-by-side heading into the final corner.
Hoy pounded down on his pedals, gritting his teeth as he tore over the final 40 metres to finish just ahead of Levy, with van Velthooven and Mulder right on their wheels.
Hoy did a victory lap before stopping on the front stretch, where he handed his bike over to his coaches and then pumped his fist while waving the British flag.
"You go to every length to tick off the boxes, but you can never be sure," Hoy said. "When you step to the podium, you realize that everything has paid off."