How ironic, though, that it had to come in defeat.
The veteran Ukrainian warrior came agonisingly close to becoming only the second fighter after George Foreman to win a recognised version of the world title as a forty-something before being stopped by Anthony Joshua at Wembley Stadium.
Bruised, battered and with a deep cut by his left eye, he could only reflect ruefully on having failed to follow up his sixth round knock-down of Joshua aggressively enough, feeling he had let the Briton off the hook.
Yet, although a 14-year age gap and Joshua's fitness, strength and power eventually saw him floored twice and finally rescued by the referee in the 11th round, Klitschko still felt like a winner at the end of an exhilarating evening.
Ninety thousand fans at Wembley seemed to agree as the man who was so often damned with faint praise during 11 years of heavyweight dominance received much greater acclaim here than he had after many of his mundane victories.
Often portrayed as being too safety-first and mechanical in approach, here was a very different 'Dr Steelhammer', stung into desperate defiance after Joshua had sent him crashing to his knees with a fifth-round assault.
It looked for all money like the end for the man who had appeared well past his sell-by-date in a sorry dethroning at the hands of Tyson Fury some 17 months earlier, but as Klitschko himself said: "I took a beating but I recovered well."
COUNTER-ATTACK
Indeed, in what was perhaps the most courageous couple of minutes in his two-decade professional career, Klitschko fought back dazzlingly, one big left hook setting up a counter-attack so ferocious that by the end of the round it was Joshua who was looking almost out on his feet.
After following up with a booming right cross in the next which saw Joshua felled for the first time in his professional career, Klitschko made what he felt was a crucial, fight-turning error.
"I thought he wouldn't get up. Big respect to AJ. From that moment, I think I should have done more straight after he went down," he said.
"But I was pretty sure it was going to be my night so I took my time."
Big mistake. Joshua was given a breather and when he clawed his way back in the later stages, finding a "second wind", his wicked body shots began to sap Klitschko's stamina, setting up the painful denouement.
As the Wembley crowd cheered him afterwards, though, Klitschko started to appreciate that the historic contest had elevated the reputations of all involved.
"I think Joshua and I both did great, I think we did a lot for the sport in the way we performed and how we respected and treated each other," he said.
"It was a great night for boxing and the fans. You will probably be surprised by my statement, but I don't feel like I lost.
"Tonight, we all won. I didn't get the belts but I didn't feel like I lost - not my name, my face, nor my reputation. It was great to be involved in such an amazing occasion."
This did not sound like a man who was quite ready to hang up his gloves and he had not looked like one either as he often outboxed his old sparring partner, teaching Joshua more in one night than he had learned in his other 18 bouts combined.
"I'll take my time over deciding what happens next," said Klitschko, whose record now stands at 64-5.
"I have a rematch clause in the contract but right now I won't make any decisions."
(Reporting by Ian Chadband, editing by Nick Mulvenney)
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