No. If there was a leak then it wouldnt pressurize properly on the way up. If it was holding pressure, it would probably keep doing so.
A famous example of this is American Airlines flight 96 (1972): https://en.wikipedia.org/wiki/American_Airlines_Flight_96
The thing that doesn't need to happen is flying at full flight altitude when the pressure differential between the inside and outside is greatest.
Still, you don’t want to take a structurally damaged plane high up.