Technically Two, or four if your Catholic. Henry's fourth marriage to Anne of Cleves was annulled. This is very different from a divorce. Legally, it means it never took place. There were two grounds to the annulment. Anne and Henry never consummated the marriage; that is, they never had intercourse. Refusal or inability to consummate a marriage is still grounds for an annulment today. In addition, Anne was also betrothed to Francis, Duke of Lorraine when she married Henry. At that time, the formal act of betrothal was a legal bar to marrying someone else. All parties agreed that no marriage took place. So that leaves five. The pope declared Henry's second marriage to be illegal because he was still married to his first wife, Cathrine of Aragon. Henry, as head of the new Church of England declared in turn that his first marriage was invalid on the legal ground that a man could not sleep with his brothers widow. The King cited the old testament, which he claimed as 'Gods Law' whether the pop like it or not. Depending on whether you believe the pope or the king this brings it down to either four or three marriages. Henry annulled his marriage to Anne Boleyn just before he had her executed for adultery. This was somewhat illogical: if the marriage never existed then Anne could not be accused of betraying it. He did the same with his fifth wife, Cathrine Howard. All the evidence suggests she was unfaithful to him before and during their marriage. This time Henry passed a special act making it treasonable for a queen to commit adultery. Once again, he also had the marriage annulled. So that makes four annulments, and only two incontestably legal marriages. Apart from Henry's last wife, Cathrine Parr (who outlived him), the lady who got off the lightest was Anne of Cleves. After their annulment, the king showered her with gifts and the official title of 'beloved sister'. She visited court often, swapping recipes and household gadgets with the other man who had never been her husband.