The Dannemora debacle

Ultimately the escapees from Dannemora failed to avoid capture for even 30 days, so the prison (officially called the Clinton Correctional Facility) can still claim that no one has successfully escaped from there in its 165-year history. It was a near thing, since if their getaway associates had done their jobs properly they may well have been in a faraway part of the country now (if not in another country).

Alcatraz still retains its place as the hardest prison to escape from. The best that anyone could manage was to reach the shore and collapse of exhaustion, which resulted in his capture within minutes.

https://en.wikipedia.org/wiki/John_Paul_Scott

Apart from that, there is no known case of anyone escaping alive and reaching the mainland. One famous case (made famous by Clint Eastwood in “Escape from Alcatraz”) remains officially unsolved as no bodies were found, but if the trio did survive some evidence should have emerged in the past 50-odd years.

https://en.wikipedia.org/wiki/June_1962_Alcatraz_escape

The final scorecard reads:

During its 29 years of operation, the penitentiary claimed that no prisoner successfully escaped. A total of 36 prisoners made 14 escape attempts, two men trying twice; 23 were caught, six were shot and killed during their escape, two drowned, and five are listed as “missing and presumed drowned”.

Britain has had its share of famous escapees who succeeded in leaving the country and were never recaptured. However they did ensure that no Axis prisoner of war could escape and return to their country.

The only German who had been imprisoned in Britain and succeeded actually escaped after he was moved to Canada.

https://en.wikipedia.org/wiki/Franz_von_Werra

There a few lesser known cases of Germans and Austrians escaping from detention in India and making their way to Tibet and Japanese-held Burma without being caught. Heinrich Harrer (“Seven Years in Tibet”) was commissioned as an SS officer (much in the same way that Tendulkar was commissioned in the IAF) so he should not really count.

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