USERELATIONSHIP to work with multiple dates

I have two tables:

• Date
• Opportunity

The Opportunity table contains many different date columns, including:

• Close Date (active relationship)
• Est. Order Date (inactive relationship)
• Created Date (inactive relationship)

Now I want to use the inactive relationships, so I have created the DAX measures below:

Sales by Est. Order Date:

CALCULATE (
    SUM ( Opportunity[actualvalue_base] );
    USERELATIONSHIP (
        Opportunity[Est. Order Date];
        'Date'[Date]
        )
)

The DAX Measure above is working as supposed for the inactive relationship for Est. Order Date , and I get the result I expected:

Now, when I try to use the Created Date column the same way - using the USERELATIONSHIP function as below it suddenly doesn't work. 

Sales Price by Created Date:

CALCULATE (
    SUM ( Opportunity[actualvalue_base] );
    USERELATIONSHIP (
        Opportunity[Created On];
        'Date'[Date]
        )
)

Am I doing anything wrong or is this due to any limitations with the function?