SQL Server 2017

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create table test ( id int
                  , gendate1 date
                  , gendate2 date
                  , gendate3 date
                  , gendate4 date
                  , gendate5 date
                  , gendate6 date
                  , gendate7 date
                  , gendate8 date
                  )
insert into test values
(1,'1/6/2019','4/6/2019','2/6/2019','3/6/2019','5/6/2019','7/6/2019','8/6/2019','10/6/2019'),
(2,'1/5/2019','4/5/2019','2/5/2019','3/5/2019','2/1/2019','7/5/2019','8/5/2019','10/5/2019')
2 rows affected

with cte1 as (
select id, 1 num, gendate1 gendate from test union all
select id, 2 num, gendate2 gendate from test union all
select id, 3 num, gendate3 gendate from test union all
select id, 4 num, gendate4 gendate from test union all
select id, 5 num, gendate5 gendate from test union all
select id, 6 num, gendate6 gendate from test union all
select id, 7 num, gendate7 gendate from test union all
select id, 8 num, gendate8 gendate from test 
),
cte2 as (
select id, num, gendate, row_number() over (partition by id order by gendate desc) rn
from cte1
where gendate <= '1/30/2019'
union all
select id, num, gendate, row_number() over (partition by id order by gendate asc) rn
from cte1
where gendate >= '1/30/2019'
)
select id, num, gendate
from cte2
where rn = 1
order by id, gendate


id
num
gendate


1
1
2019-01-06

1
3
2019-02-06

2
1
2019-01-05

2
5
2019-02-01