If a single effect would delete multiple Digimon, can I activate this card's "when [...] would be deleted" effect for each deletion?
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Yes, you can. For example, if your opponent activates an "if your opponent has as many or more total Digimon and Tamers as you, delete 1 of your opponent's highest level Digimon. Then, delete 1 of your opponent’s lowest level Digimon" effect, you can activate this card's "when [...] would be deleted" effect for the 1st deletion, then you can activate this card's "when [...] would be deleted" effect for the 2nd deletion that was activated by your opponent.
Source: EX1-073 Machinedramon