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You have a Fighter with the "Tunnel Fighter" fighting style (bonus action to get attacks of opportunity without using reaction & reaction to hit enemy moving more than 5ft while inside reach) and the Polearm Master feat (attack of opportunity when enemy enters reach). The Fighter has a Whip (10ft reach) and a Quarterstaff (5ft reach, polearm).

An enemy moves towards the fighter, who has activated his Tunnel Fighter stance. The enemy enters the Fighter's Whip reach, then his Quarterstaff's reach. At this precise moment, is it true that the following can happen ?

  1. The enemy, now entering the Quarterstaff's reach, gets an Attack of Opportunity from the Fighter, who does not spend his reaction thanks to his stance,
  2. Then, as the enemy moved (more than?) 5ft inside the Whip's range, the Fighter can use his reaction to attack him a second time thanks to his stance.

My hesitation comes from the fact that the Tunnel Fighter's non-AoO reaction seems to demand more than 5ft of in-reach movement, which the enemy would technically not grant if moving from exactly 10ft away to exactly 5ft away.

The question also applies for the reverse scenario : an adjacent enemy moving outside the Quarterstaff's reach (AoO without reaction) and inside the Whip's reach (non-AoO reaction) at the same time. Note that this would not require the Polearm master feat to happen.

Anti-cheese notice : while the Polearm Master feat doesn't explicitly say that the reach-entering attack-of-opportunity must be done with the polearm, it would be logical to think it was implied, so the enemy shouldn't get another attack of opportunity when entering the Whip's reach (before strike #1). Else, this already strong combo would be ridiculous.

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    \$\begingroup\$ [Related] Tunnel Fighter & Polearm Master : Indefinite Attacks of Opportunity? \$\endgroup\$ – SevenSidedDie Nov 27 '17 at 21:53
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    \$\begingroup\$ (Though that question's answers might incidentally/accidentally answer this, I'm pretty sure this is still a distinct question since the other question isn't about the precise triggering of the opportunity attacks. Answers to this are likely to cover similar but different ground.) \$\endgroup\$ – SevenSidedDie Nov 27 '17 at 21:55
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    \$\begingroup\$ Regarding your endnote about cheese, no need to worry: you can cite this answer or its source to eliminate that concern. \$\endgroup\$ – SevenSidedDie Nov 27 '17 at 22:00
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Yes

As you have mentioned, Tunnel Fighter specifically mentions that it requires more than 5 feet of movement to trigger. I see no reason that we would disregard that statement. However the PHB entry for AoO would seem to imply logically that, in fact, the quarterstaff attack would have happened just after the creature enters your reach:

You can make an opportunity attack when a hostile creature that you can see moves out of your reach. To make the opportunity attack, you use your reaction to make one melee attack against the provoking creature. The attack occurs right before the creature leaves your reach.

emphasis mine

Even though this example is in the standard AoO case of an enemy leaving your reach, there seems to be no reason to believe that the reverse would also be true and that the enemy would be less than 5 feet away from you when you AoO with your quarterstaff.

This means then that the conditions for your Tunnel Fighter ability are indeed triggered, and that you can then attempt to make that attack as well. There do not appear to be any general or specific rules that would prohibit multiple things happening based on multiple triggers and your character definitely has the actions to perform it so there seems to be nothing that would prevent this from being perfectly legal.

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