Might be a bit lengthy but hopefully clear enough.
with a as
(select -- order and number rows in table A in some way
row_number() over (order by UpperLimit) as RnA,
*
from #a),
b as
(select -- order and number rows in table B in the same way
row_number() over (order by Amount) as RnB,
*
from #b),
m as
(select -- get and number all possible pairs of values from both tables considering the restriction
row_number() over (order by a.UpperLimit desc, b.Amount desc) as RnM,
*
from a
join b on
b.Amount < a.UpperLimit),
r as
(select -- use recursion to get all possible combinations of the value pairs with metrics of interest for comparison
convert(varchar(max), RnA) as ListA,
convert(varchar(max), RnB) as ListB,
RnA,
RnB,
1 as CountB,
convert(int, Amount) as SumB
from m
where RnM = 1
union all
select
r.ListA + ' ' + convert(varchar(max), m.RnA),
r.ListB + ' ' + convert(varchar(max), m.RnB),
m.RnA,
m.RnB,
r.CountB + 1,
r.SumB + convert(int, m.Amount)
from m
join r on
m.RnA < r.RnA and
m.RnB < r.RnB),
e as
(select top(1) -- select combinations of interest using metrics
ListA,
ListB
from r
order by CountB desc, SumB desc),
ea as
(select -- turn id list into table for table A
ea.Rn,
ea.Value
from e
cross apply(select row_number() over (order by (select null)) as Rn, Value from string_split(e.ListA, ' ')) as ea),
eb as
(select -- turn id list into table for table B
eb.Rn,
eb.Value
from e
cross apply(select row_number() over (order by (select null)) as Rn, Value from string_split(e.ListB, ' ')) as eb)
select -- get output table with actual values from the original tables
a.UpperLimit,
b.Amount,
b.Id
from ea
join eb on
ea.Rn = eb.Rn
join a on
ea.Value = a.RnA
join b on
eb.Value = b.RnB;