I think we're getting there.
It's a little tough to tell where your column breaks are for the second table, but I interpreted the 1999 data as being 3 rows by 3 columns, with 1999 in each of the 3 cells in the first row; the 3 cells in the second row being "90%", "Gross", and "Up" respectively; and the third row being 10.5, 11, and 10.05 respectively.
As such, I added a row to concatenate the year, %, and the words "Gross" and "Up", using =A11&" "&TEXT($A$12,"0%")&" "&B12&" "&C12, where A11 was the year, A12 the percent, B12 Gross, and C12 Up.
Then, I used =HLOOKUP(A2&" "&B2,$A$10:$L$13,4,0) to look up the Date, %, and "Gross Up" from the first table against the second table (range $A$10:$L$13 in my sheet, which is the 3 rows you had plus the concatenation as described above)
Does that help?