| 2026-07-10 | Not be square with |
| 2026-06-15 | Come up short money-wise |
| 2026-04-30 | Be left at a loss? |
| 2026-04-27 | Have debts |
| 2026-04-02 | Be shy |
| 2026-03-30 | Be in arrears |
| 2026-03-21 | Be behind |
| 2026-02-03 | Have debts |
| 2026-01-20 | Be behind |
| 2025-09-24 | Carry a debt |
| 2025-06-18 | "You ___ me!" |
| 2025-05-11 | "I ___ you!" |
| 2025-04-16 | Be in debt |
| 2025-02-24 | Have debt |
| 2024-07-01 | The "o" of i.o.u. |
| 2024-05-28 | Be indebted to |
| 2024-05-13 | Have debts |
| 2024-04-18 | Be beholden to |
| 2024-04-09 | Have trouble with one's balance? |
| 2024-02-01 | Need to pay |
| 2023-12-11 | Have debts |
| 2023-11-07 | Have bills due |
| 2023-10-23 | Be in the red |
| 2023-09-29 | Need to pay |
| 2023-08-02 | Be beholden to |
| 2023-07-28 | Be shy |
| 2023-07-19 | Not be square, say |
| 2023-04-24 | Be in debt |
| 2023-02-23 | Be behind, in a way |
| 2023-01-03 | Be in the red |
| 2022-08-10 | Carry a balance |
| 2021-10-07 | Be shy |
| 2021-10-06 | Be in a red state, perhaps |
| 2021-10-05 | What the middle of 58-Across stands for |
| 2021-08-23 | Have debts |
| 2021-08-22 | Word repeated in "I ___, I ___, it's off to work I go" |
| 2021-06-23 | Fall short |
| 2021-06-14 | Be in debt |
| 2021-05-11 | Have to pay |
| 2021-05-02 | Be short |
| 2020-11-08 | Word that sounds like its first letter |
| 2020-10-12 | Have debts |
| 2020-09-14 | Be in debt |
| 2020-07-16 | Be short |
| 2020-06-23 | Be behind, in a way |
| 2020-05-18 | Be indebted to |
| 2020-04-14 | Not be up to date on bills |
| 2020-02-12 | "You ___ me one" |
| 2020-02-06 | Be attributable (to) |
| 2020-01-06 | Be in debt |
| 2019-12-02 | Be obligated to |
| 2019-07-10 | Be shy |
| 2019-06-26 | Be behind |
| 2019-06-02 | Be short |
| 2019-05-15 | Have obligations |
| 2019-03-17 | Get a Venmo request, say |
| 2018-12-09 | Be beholden to |
| 2018-11-13 | Fall behind |
| 2018-10-23 | What debtors do |
| 2018-10-08 | "You ___ me one" |
| 2018-07-11 | Be behind |
| 2018-02-10 | Fall behind |
| 2017-09-11 | Have debts |
| 2017-09-08 | "How much do I ___?" |
| 2017-08-17 | Be in the red |
| 2017-08-01 | Be in the red |
| 2017-06-02 | Be short |
| 2017-03-20 | Have debts |
| 2017-03-05 | Be behind |
| 2017-02-19 | Fall behind |
| 2017-01-23 | Have bills |
| 2017-01-16 | Have a mortgage, e.g. |
| 2016-08-17 | Carry a balance |
| 2016-08-13 | What many do at tax season |
| 2016-06-29 | Have bills |
| 2016-03-17 | Have a bill, say |
| 2016-03-09 | See red? |
| 2016-03-04 | Be short |
| 2016-03-02 | Be in hock |
| 2015-12-24 | "I ___ you" |
| 2015-09-17 | Put off paying |
| 2015-09-01 | "You ___ me one" |
| 2015-06-06 | Not be settled with |
| 2015-05-26 | Have obligations |
| 2015-05-03 | Be behind |
| 2015-02-09 | Have to fork over |
| 2014-12-22 | Be behind in bills |
| 2014-12-21 | Get behind |
| 2014-07-03 | Must give |
| 2014-04-17 | "I ___ you" |
| 2014-04-03 | Not be squared up, say |
| 2014-02-02 | Have debts |
| 2014-01-01 | Have a mortgage, say |
| 2013-11-19 | Have creditors |
| 2013-11-17 | Get behind |
| 2013-10-27 | Have a balance |
| 2013-10-01 | "I ___ you one" |
| 2013-08-22 | Be obliged |
| 2013-07-20 | End up short |
| 2013-04-26 | Not be square with |
| 2012-10-23 | Part of i.o.u. |
| 2012-07-15 | "I ___ you one" |
| 2012-06-24 | Have loans |
| 2012-06-07 | Be behind |
| 2012-06-03 | Not be entirely independent |
| 2012-04-17 | Have bills |
| 2012-02-16 | "You ___ me" |
| 2012-01-03 | Be in debt to |
| 2011-11-29 | Run a tab |
| 2011-06-16 | Be shy |
| 2011-05-14 | What unsettled people do? |
| 2011-05-09 | Be in debt |
| 2011-03-15 | Have bills |
| 2011-01-30 | Be shy |
| 2010-12-28 | Have payables |
| 2010-12-08 | Be short |
| 2010-11-16 | "I ___ you one!" |
| 2010-10-03 | Be behind |
| 2010-05-23 | Fall behind |
| 2010-04-05 | Fall behind financially |
| 2010-03-25 | Get behind |
| 2009-11-17 | Run a tab |
| 2009-07-17 | Have yet to settle |
| 2009-05-14 | "You ___ me!" |
| 2009-04-05 | Be short |
| 2009-01-14 | Be in the red |
| 2008-11-08 | Come up short |
| 2008-03-18 | Be in hock |
| 2008-01-28 | Be in the red |
| 2007-07-10 | Be short |
| 2007-06-19 | Have a tab |
| 2007-04-06 | Be outstanding? |
| 2006-12-17 | Be in a hole |
| 2006-11-21 | See red? |
| 2006-11-12 | Have bills to pay |
| 2006-11-05 | Show a deficit |
| 2006-10-30 | Have bills |
| 2006-09-16 | Have to return |
| 2006-08-26 | Be short |
| 2006-08-13 | Fall behind |
| 2006-03-13 | Be in the red |
| 2006-02-20 | Have bills due |
| 2005-10-18 | Have a tab |
| 2005-05-22 | Have bills |
| 2005-05-17 | See red? |
| 2005-05-12 | Be shy |
| 2004-12-30 | Need dough |
| 2004-10-04 | Be behind in payments |
| 2004-07-28 | See red? |
| 2004-04-11 | Need to pay |
| 2004-02-11 | Be in the hole |
| 2004-02-04 | Be in the red |
| 2004-01-20 | Have markers out |
| 2003-09-24 | Have a mortgage |
| 2003-05-04 | "I ___ you one" |
| 2002-12-19 | Need to pay |
| 2002-08-30 | What borrowers do |
| 2002-05-28 | Be beholden to |
| 2002-04-08 | Be indebted to |
| 2002-01-27 | Really should give |
| 2001-12-06 | Postpone paying |
| 2001-10-18 | Part of i.o.u. |
| 2001-06-07 | "To what do I ___ ...?" |
| 2001-05-10 | "You ___ it to yourself" |
| 2001-04-22 | Be behind |
| 2001-01-14 | Be beholden to |
| 2000-06-21 | Be in the red |
| 2000-04-28 | See red? |
| 2000-03-13 | Have debts |
| 2000-02-09 | Be light, in poker |
| 1999-12-27 | Have bills |
| 1999-10-21 | Be behind |
| 1999-09-06 | Be indebted to |
| 1999-08-03 | Be in debt to |
| 1999-04-05 | Be in the red |
| 1999-02-28 | Be attributable (to) |
| 1998-11-09 | Have a debt |
| 1998-11-04 | Be in arrears |
| 1998-10-28 | Have to pay back |
| 1998-10-01 | Part of 52-Across |
| 1998-08-26 | Have chits out |
| 1998-07-13 | Be indebted to |
| 1998-05-06 | See red? |
| 1998-04-19 | "To what do I ___..." |
| 1998-03-20 | See red? |
| 1998-03-10 | Have bills |
| 1998-03-01 | Need to reimburse |
| 1998-02-04 | Have chits out |
| 1998-01-19 | Be in arrears |
| 1997-09-18 | Have a tab |
| 1997-09-02 | Be in debt |
| 1997-05-29 | Take credit? |
| 1997-05-21 | Be in hock |
| 1997-04-20 | Have markers out |
| 1997-01-02 | Have bills |
| 1996-10-17 | Have bills |
| 1996-05-14 | Have bills |
| 1995-10-29 | Be beholden to |
| 1995-09-24 | Be in for |
| 1995-08-06 | Be beholden to |
| 1995-04-26 | Be in the red |
| 1995-04-16 | Part of 59-Across |
| 1995-02-07 | Be in the red |
| 1994-11-10 | See red? |
| 1994-06-19 | Be in the red |
| 1994-03-10 | Be in the red |
| 1993-12-13 | Have a tab |