SQL Server 2017

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create table ILR (LEARNERID int, LEARNSTARTDATE datetime);
insert into ILR values(1, '2019-09-01');
insert into ILR values(2, '2020-05-06');
insert into ILR values(3, '2020-08-05');
insert into ILR values(4, '2019-08-01');
insert into ILR values(5, '2019-07-31');
5 rows affected

select LEARNERID, LEARNSTARTDATE, EndYear - 1 StartYear, EndYear
from (
  select LEARNERID, LEARNSTARTDATE, year(dateadd(month, 5, LEARNSTARTDATE)) EndYear
  from ILR  
) t  


LEARNERID
LEARNSTARTDATE
StartYear
EndYear


1
2019-09-01 00:00:00.000
2019
2020

2
2020-05-06 00:00:00.000
2019
2020

3
2020-08-05 00:00:00.000
2020
2021

4
2019-08-01 00:00:00.000
2019
2020

5
2019-07-31 00:00:00.000
2018
2019


select LEARNERID, LEARNSTARTDATE,
  format((EndYear - 1) % 100, '00') + '/' + format((EndYear) % 100, '00') AcademicYear
from (
  select LEARNERID, LEARNSTARTDATE, year(dateadd(month, 5, LEARNSTARTDATE)) EndYear
  from ILR  
) t  


LEARNERID
LEARNSTARTDATE
AcademicYear


1
2019-09-01 00:00:00.000
19/20

2
2020-05-06 00:00:00.000
19/20

3
2020-08-05 00:00:00.000
20/21

4
2019-08-01 00:00:00.000
19/20

5
2019-07-31 00:00:00.000
18/19

LEARNERID	LEARNSTARTDATE	StartYear	EndYear
1	2019-09-01 00:00:00.000	2019	2020
2	2020-05-06 00:00:00.000	2019	2020
3	2020-08-05 00:00:00.000	2020	2021
4	2019-08-01 00:00:00.000	2019	2020
5	2019-07-31 00:00:00.000	2018	2019

LEARNERID	LEARNSTARTDATE	AcademicYear
1	2019-09-01 00:00:00.000	19/20
2	2020-05-06 00:00:00.000	19/20
3	2020-08-05 00:00:00.000	20/21
4	2019-08-01 00:00:00.000	19/20
5	2019-07-31 00:00:00.000	18/19