Which Men Might have Beaten Sherlock Holmes Early in his Career?

I figured it was about time I posted another article here.  First, to celebrate the first year of the blog, and, second, to honour Sherlock Holmes’ 159th birthday.

In the short story, ‘The Five Orange Pips,’ Holmes indicates, “I have been beaten four times – three times by men and once by a woman,” but we are only explicitly told the identity of the woman, Irene Adler.  Who might the three men be?  Several hints to the possible identity of one of these are given in ‘The Red-Headed League.’

In referring to this person, Holmes discloses, “He is, in my judgment, the fourth smartest man in London, and for daring I am not sure that he has not a claim to be third.  I have known something of him before.”  Later in the story Holmes says, “I’ve had one or two little turns also with [him], and I agree with you that he is at the head of his profession.”  Next, Holmes remarked that he had an ingenious mind.  Also, he declared that this person was “one of the coolest and most daring criminals in London.”  Based upon these statements, this mystery man may have been one of the group of three alluded to earlier in this post.  I refer, of course, to Mr. John Clay aka Vincent Spaulding, Jabez Wilson’s able assistant at his pawnbroker shop.

Any guesses on the other two anyone?  Keep in mind these cases must have taken place before ‘The Five Orange Pips’ unless Watson once again fell into the old habit of telling his stories wrong end foremost.

Thank you all for reading this.  Happy birthday, Sherlock Holmes!