-- one more test data row

INSERT INTO MyTestTable (ID, Col1) SELECT 4, 'a longer string value1 / a much much much much longer string value2 / whatever / whatever / whatever'

SELECT

Col1,

LEFT(Col1, position_of_first_slash - 1) AS Value1,

SUBSTRING(Col1, position_of_first_slash + 1, CHARINDEX('/', Col1, position_of_first_slash + 1) - position_of_first_slash - 1) AS Value2

FROM dbo.MyTestTable

CROSS APPLY (

SELECT CHARINDEX('/', Col1) AS position_of_first_slash

) AS ca1

WHERE

Col1 LIKE '%/%/%'