The man, known only as LE, continued to fight the case through the High Court and Court of Appeal despite being thrown out of the country more than two years ago.
Judges have now ruled that part of the time he was locked up was technically unlawful because there was a failure to carry out monthly reviews of his custody - but that even if they had been he would have remained behind bars.
The 47-year-old had spent 20 years in Britain and served a seven-year jail term for plotting kidnap and blackmail before the Home Office managed to deport him, all the while running up huge taxpayer-funded legal bills for a string of court and tribunal hearings.
LE arrived in the UK as a visitor in 1989 but was allowed to stay on indefinitely, even after his marriage to a British citizen broke down, the Court of Appeal heard.
In 1995 he was charged with having crack cocaine with intent to supply and obtaining a false passport by deception but was deemed mentally unfit to stand trial after being diagnosed as a paranoid schizophrenic, and he spent two and a half years in a mental hospital.
He was convicted of conspiracy to kidnap and blackmail in 2002 and was sentenced to a seven-year jail term, making his first claim for asylum whilst he was behind bars.
LE was informed of the Home Office's intention to deport him as long ago as February 2006, but a series of court challenges followed and directions for his removal from the country twice had to be cancelled, once after an intervention by his local MP.
Further confusion followed after he lodged an application with the European Court of Human Rights without telling his solicitors and the Jamaican High Commission responded by refusing to endorse an emergency travel document.
Even after he was freed from detention on bail in July 2007, the legal process continued to grind onwards and LE was not finally removed from the UK until December 2009.
Despite not even being in the country, LE carried on his fight against the Home Office, claiming he had been unlawfully detained between February 2006 and July 2007.
His legal team fought his case through the High Court and the Court of Appeal and have now won a ruling that, as there was a failure to carry out monthly reviews of his custody, his detention was unlawful for about seven months in 2006.
However, awarding LE just £1 damages, Lord Justice Richards, sitting with Lords Justice Maurice Kay and Kitchin, said his initial detention was lawful and, even had the reviews been carried out as they should have been, he would inevitably have been kept inside.
