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In my opinion, if his last match is at a WrestleMania, he should win it to preserve the streak and legacy. Then he could be destroyed by a load of heels and buried/put in a coffin. Plus it leaves the door open if a few years down the line Vince wants Undertaker back, he CAN come back with little/no damage to his credibility.
If his last match isn't a WrestleMania, however, he should job. In a destruction scenario like Pyro-Maniac suggested with Kane, or some other deserving Superstar.
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