FunkyMonk,
I believe this code is flawed in that it violates two of the rules.

• The maximum match must be taken.
• Entire word can not be matched

Changing the players for a dictionary file, I tried 'hello'. It produced the following:

h.ello
  PREFIX h: ha haberdasher ..... he head
[download]

Neither 'he' nor 'head' should be matched here because they share more than just 'h' in common with 'hello'. 'he' should be excluded because it consumes the entire word.