So, I went back to my good old SQL Server, started Query Profiler on the Tridion DB and found my answer. **When using multiple search terms, the SQL IN operator is used, and the Tridion Criteria.Like operator is ignored!!!** In particular look at this snippet from the full code: searchArray = Array.ConvertAll(searchArray, x => "%" + x.Trim() + "%"); var criteria = new List<Criteria> { new KeywordCriteria(_subjectCategory, searchArray, Criteria.Like), new KeywordCriteria(_syllabusCategory, searchArray, Criteria.Like) }; As you can see I did the following to set up a LIKE search for each term of the searchArray = { "Physics", "0625" } in this particular case 1. Put "%" wilcard at start and end of each search term 2. Used the Criteria.Like operator on both my criteria Well, here is what I got in Query Profiler: declare @p1 int set @p1=1 exec sp_prepexec @p1 output,N'@P0 int,@P1 nvarchar(4000), @P2 nvarchar(4000),@P3 nvarchar(4000), @P4 nvarchar(4000),@P5 nvarchar(4000),@P6 nvarchar(4000)', N'select distinct top 10000 itemmeta0_.PUBLICATION_ID as col_0_0_, itemmeta0_.ITEM_REFERENCE_ID as col_1_0_, itemmeta0_.ITEM_TYPE as col_2_0_, itemmeta0_.TITLE as col_3_0_ from ITEMS itemmeta0_ cross join ITEM_CATEGORIES_AND_KEYWORDS relatedkey1_ where itemmeta0_.PUBLICATION_ID=@P0 and ( relatedkey1_.ITEM_REFERENCE_ID=itemmeta0_.ITEM_REFERENCE_ID and relatedkey1_.PUBLICATION_ID=itemmeta0_.PUBLICATION_ID and relatedkey1_.CATEGORY=@P1 and (relatedkey1_.KEYWORD in (@P2 , @P3)) or relatedkey1_.ITEM_REFERENCE_ID=itemmeta0_.ITEM_REFERENCE_ID and relatedkey1_.PUBLICATION_ID=itemmeta0_.PUBLICATION_ID and relatedkey1_.CATEGORY=@P4 and (relatedkey1_.KEYWORD in (@P5 , @P6)) ) order by itemmeta0_.TITLE ASC', 163,N'TSL Subjects',N'%Physics%',N'%0625%', N'TSLSyllabus',N'%Physics%',N'%0625%' select @p1 So, Tridion Content has actually broken my query by allowing me to enter wildcards, but then silently substituting the Criteria.Like with a SQL IN operator: and (relatedkey1_.KEYWORD in (@P2 , @P3)) OUR SOLUTION: We are going to restructure our Subject Category to include Subjects + Code, and then do a LIKE on a single search term eg "%Physics 0625%". Happy to hear if anyone has got any alternative suggestions.