for contract_number in {1..50}
do printf "%s;%s\\n%s%s\\n" "$contract_number" "$team-member1" "$contract_number" "$team-member2"
done

# prints something like:
#1;john-doe@example.com
#1;jane-doe@example.com
#2;john-doe@example.com
#2;jane-doe@example.com