SQL Server 2022

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create table myTable (Company varchar(10),	ContractNo varchar(10),	Gender varchar(10),	Month varchar(10));
insert into myTable (Company,ContractNo,Gender,Month) values 
('ITV',	'cont1',	'male',	'aug'),
('ITV',	'cont1',	'male',	'feb'),
('ITV',	'cont1',	'female',	'jan'),
('ITV',	'cont1',	'male',	'dec'),
('ITV',	'cont1',	'female',	'apr'),
('C4',	'cont1',	'male',	'sept');

with data as (
  select Company, ContractNo, Gender, Month, row_number() over (partition by Company,ContractNo,Gender 
  order by case 
       when Month='jan' then 1
       when Month='feb' then 2
       when Month='mar' then 3
       when Month='apr' then 4
       when Month='may' then 5
       when Month='jun' then 6
       when Month='jul' then 7
       when Month='aug' then 8
       when Month='sep' then 9
       when Month='nov' then 10
       when Month='oct' then 11
       when Month='dec' then 12
       end
      ) as RowNo
from myTable),
  maleData as (select Company, ContractNo, Gender, Month, RowNo 
      from data 
      where Gender = 'male'),
  femaleData as (select Company, ContractNo, Gender, Month, RowNo 
      from data
      where Gender = 'female')
select coalesce(m.Company, f.Company) Company,
  coalesce(m.ContractNo, f.ContractNo) ContractNo,
  m.Gender MaleGender, 
  m.Month MaleMont,
  f.Gender FemaleGender, 
  f.Month FemaleMonth
from maleData m
  full join femaleData f on m.Company = f.Company and
    m.ContractNo = f.ContractNo and
    m.RowNo = f.RowNo;

Company	ContractNo	MaleGender	MaleMont	FemaleGender	FemaleMonth
C4	cont1	male	sept	null	null
ITV	cont1	male	feb	female	jan
ITV	cont1	male	aug	female	apr
ITV	cont1	male	dec	null	null