You get an injury and replace him. Later on in the same game that player gets injured too.

How often does this happen to you?

I get it a 2 or 3 times a season which seems unrealistic to me.

It happens so hardly unrealistic.

I went through 4 years at FC Bayern without a major injury in that whole time, then I took the Milan job and currently have Toni, Owen, Ottl, Tolalan, Aguero and Cassanni out with something broken in the leg area.

Look at West Ham they have had numerous injuries alls eason.

never had two players in the same position injured in the same match... had player injured ans the sub i brought on for him get injured too.. and irl, look at west ham (as nomis said) or newcastle (who have struggled with injuries as long as i can remember)

You just are damn lucky, I guess.

From what I understand there are rather a lot kind of injuries and I assume that some random generator picks one for you.

However, if rather many players are receiving the same type of injury again and again, then you should inspect your training schedules. Odds are high you’re overtraining them a little.

Once in four seasons, then twice in pre-season on my 5th. Not bad IMO. Two months in and no repeat.

I've had the same opposition player break bones for 2 of my players in the same match and leave 3 others playing on with 'green injuries'. The little git came out without even a yellow card, too.
To answer the original question; yes, a few times.

its happened a few times to me but i dont think it is unrealistic

Only two players from the same position?
Trust me, you got off lightly.

In a network game i had 3 RBs injured for 4 months.

In my long term FM07 game i had 3 GKs out for 3 months.

Now, it happens irl, however - i was beyond furious when my 3rd GK got injured - mainly because he got injured in training. IRL if you had 2 GKs out, the 3rd would be wrapped in cotton wool.
But i appreciate it is not a common enough occurance to warrant SI coding such a scenario.