Historical clue formulations

• Not be square with — 2026-07-10
• Come up short money-wise — 2026-06-15
• Be left at a loss? — 2026-04-30
• Have debts — 2026-04-27
• Be shy — 2026-04-02
• Be in arrears — 2026-03-30
• Be behind — 2026-03-21
• Have debts — 2026-02-03
• Be behind — 2026-01-20
• Carry a debt — 2025-09-24
• "You ___ me!" — 2025-06-18
• "I ___ you!" — 2025-05-11
• Be in debt — 2025-04-16
• Have debt — 2025-02-24
• The "o" of i.o.u. — 2024-07-01
• Be indebted to — 2024-05-28
• Have debts — 2024-05-13
• Be beholden to — 2024-04-18
• Have trouble with one's balance? — 2024-04-09
• Need to pay — 2024-02-01
• Have debts — 2023-12-11
• Have bills due — 2023-11-07
• Be in the red — 2023-10-23
• Need to pay — 2023-09-29
• Be beholden to — 2023-08-02
• Be shy — 2023-07-28
• Not be square, say — 2023-07-19
• Be in debt — 2023-04-24
• Be behind, in a way — 2023-02-23
• Be in the red — 2023-01-03
• Carry a balance — 2022-08-10
• Be shy — 2021-10-07
• What the middle of 58-Across stands for — 2021-10-05
• Have debts — 2021-08-23
• Word repeated in "I ___, I ___, it's off to work I go" — 2021-08-22
• Fall short — 2021-06-23
• Be in debt — 2021-06-14
• Have to pay — 2021-05-11
• Be short — 2021-05-02
• Word that sounds like its first letter — 2020-11-08
• Have debts — 2020-10-12
• Be in debt — 2020-09-14
• Be short — 2020-07-16
• Be behind, in a way — 2020-06-23
• Be indebted to — 2020-05-18
• Not be up to date on bills — 2020-04-14
• "You ___ me one" — 2020-02-12
• Be attributable (to) — 2020-02-06
• Be in debt — 2020-01-06
• Be obligated to — 2019-12-02