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Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without is ad infinitum. It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too. The PH lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules¹ you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them. But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

Ability checks are something the DM asks for, if there is chance involved. Else the DM can just decree the outcome.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep. (Even if they want to stay awake, they might auto-fail, depending on how the DM rules²).

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH). Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

¹ There are also optional rules in Xanathar's that, as explained in this answer use saving throws instead of ability checks, and might work more in your favor.

² It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep. (See also Is it possible to fail an ability check on purpose? for more on failing ability checks).

Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without ad infinitum. It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too. The PH lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules¹ you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them. But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep. (Even if they want to stay awake, they might auto-fail, depending on how the DM rules²).

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH). Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

¹ There are also optional rules in Xanathar's that, as explained in this answer use saving throws instead of ability checks, and might work more in your favor.

² It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep. (See also Is it possible to fail an ability check on purpose? for more on failing ability checks).

Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without is ad infinitum. It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too. The PH lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them. But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

Ability checks are something the DM asks for, if there is chance involved. Else the DM can just decree the outcome.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep.

It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep. (See also Is it possible to fail an ability check on purpose? for more on failing ability checks).

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH). Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either. It certainly is not a hard rules mechanic, and thus is something the DM must interpret.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

(There are also optional rules in Xanathar's that, as explained in this answer instead use saving throws, and might work more in your favor).

Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without is ad infinitum. It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too. The PH lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules¹ you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them. But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

Ability checks are something the DM asks for, if there is chance involved. Else the DM can just decree the outcome.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep. (Even if they want to stay awake, they might auto-fail, depending on how the DM rules²).

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH). Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

¹ There are also optional rules in Xanathar's that, as explained in this answer use saving throws instead of ability checks, and might work more in your favor.

² It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep. (See also Is it possible to fail an ability check on purpose? for more on failing ability checks).

Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without is ad infinitum.

  It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too.

  The PH also lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them.

  But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

See this question about Is it possible to fail an ability check on purpose? — ability checks are something the DM asks for, if there is chance involved. Else the DM can just decree the outcome.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep.

It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep.

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH. Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either. It certainly is not a hard rules mechanic, and thus is something the DM must interpret.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

(There are also optional rules in Xanathar's that, as explained in this answer instead use saving throws, and might work more in your favor).

Unlikely, as it only works if neither of you falls asleep

The PH states on p. 186 under Resting:

Heroic though they might be, adventurers can’t spend every hour of the day in the thick of exploration, social interaction, and combat. They need rest—time to sleep and eat

So it's pretty clear that the default assumption is that creatures need rest and cannot just keep up without is ad infinitum. It still might be possible with a conscious effort to do so — the real-world record for going without sleep is 11 days. For this there are some rules, too. The PH lists this under constitution checks:

The DM might call for a Constitution check when you try to accomplish tasks like the following: […]

• Go without sleep

Under the core rules you only can keep this up if your DM does not impose such checks upon you, or if you succeed on them. But more importantly, it works only if they rule that the victim who cannot take actions does not fall asleep either.

Ability checks are something the DM asks for, if there is chance involved. Else the DM can just decree the outcome.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

It is up to the victim to decide if they want to fight their need to sleep. If they do not, they would just fall asleep.

It's not clear if the check to remain awake actually would require an action, not all of them do. If the DM decided it would, the victim cannot succeed, even if it decides to fight the natural need to sleep, because it cannot take the action, and it will fall asleep. (See also Is it possible to fail an ability check on purpose? for more on failing ability checks).

Mechanically, the Incapacitated condition only restricts your ability to take actions. It doesn't say that it blocks you from thinking or taking decisions. Dazed is not a defined condition (in fact, this is the only time the term is used in the PH). Its dictionary definition is (Oxford Languages):

unable to think or react properly

While this may impair your thinking and decision making, for example for formulating complex plans, this is not a condition that would stop you from naturally falling asleep either. It certainly is not a hard rules mechanic, and thus is something the DM must interpret.

So, it seems unlikely this will work, not primarily because you have to stay awake, but because you have no way to force your victim to stay awake.

(There are also optional rules in Xanathar's that, as explained in this answer instead use saving throws, and might work more in your favor).