It really isn't possible to do that to the modern subs in DW, because they usually have towed array sonar, which allows them to see directly behind them. You can get close, but nothing like the 200m close trails you are thinking of. For subs without towed arrays: Hans, Xias, and pretty much all of the desiel submarines (assuming you are using LWAMI), you just need to get directly behind them, and speed up until you are as close as desired, at which point you can simply follow them visually on HF sonar, which would allow you to see their depth.
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