Answer:
Yes it is possible for the pressure to increase if head loss occurs in a pipe due to sudden enlargement.
Explanation: Consider the attached figure
The head loss in a pipe due to sudden enlargement is given by

where
is the velocity in the smaller pipe
is the velocity in the larger pipe
Now by Bernoulli's theorm between the 2 points in the pipe we have

In the above equation we can see that
for
we have

thus pressure increases