Lifelink is a static ability that causes life gain equal to the amount of damage the source deals, regardless of how many creatures or players it damages (CR 702.15b). The life is gained as a single event equal to the total damage dealt by that source in that instance.
When a creature with lifelink attacks and is blocked by multiple creatures (via a 'block by multiple' situation or if the attacker somehow deals damage to multiple blockers), the controller gains life equal to the total damage dealt across all those creatures. Each point of damage dealt triggers the lifelink effect collectively, not separately per creature (CR 702.15b, 119.3).
It is important to note that the combat damage is all dealt simultaneously during the combat damage step (CR 510.2). So all damage to all blockers is counted together, and you gain that total as one life-gain event.
Example: Your 4/4 creature with lifelink is blocked by two 1/1 creatures. You assign 1 damage to each blocker (using trample or similar isn't needed; assume you can split damage). You deal 2 total damage, so you gain 2 life — 1 for each blocker hit — all at once.
Note: A creature normally deals combat damage only to the creature blocking or being blocked by it. If your attacker is blocked by two creatures and you assign damage to both (CR 510.1c allows the attacking player to divide combat damage among multiple blockers), lifelink counts all damage assigned and dealt.
Unofficial fan resource — not affiliated with or endorsed by Wizards of the Coast. Answers are AI-generated estimates grounded in the Comprehensive Rules and are not a substitute for an official judge. Verify anything match-critical.