I think you need first reshape df2 and then merge with left join with df1:
df2 =df2.set_index('Len/Bar').unstack().rename_axis(('Bar','Len')).reset_index(name='Amount')
df2 = df1.merge(df2, how='left', on=['Len', 'Bar'])
print (df2)
  Len Bar  Amount
0   x   a       4
1   y   a       2
2   z   a       6
3   x   b       2
4   y   b       7
5   z   b       3
6   x   c       8
7   y   c       7
8   z   c       9
Another solution:
df2 = df2.set_index('Len/Bar').stack().rename_axis(('Bar','Len')).rename('Amount')
df2 = df1.join(df2, on=['Len', 'Bar'])
print (df2)
  Len Bar  Amount
0   x   a       4
1   y   a       2
2   z   a       6
3   x   b       2
4   y   b       7
5   z   b       3
6   x   c       8
7   y   c       7
8   z   c       9
EDIT:
If you dont know if need merge/join it depends if need filter reshaped df2 by df1 or not.
See difference:
#removed some rows
print (df1)
  Len Bar
0   x   a
1   y   a
2   z   a
3   x   b
4   y   b
print (df2)
  Bar Len  Amount
0   a   x       4
1   a   y       2
2   a   z       6
3   b   x       2
4   b   y       7
5   b   z       3
6   c   x       8
7   c   y       7
8   c   z       9
And after merge rows are filtered by columns Len and Bar from df1:
print (df3)
  Len Bar  Amount
0   x   a       4
1   y   a       2
2   z   a       6
3   x   b       2
4   y   b       7