| 2026-02-17 | Boot out of Europe? |
| 2025-08-19 | Winner of four World Cups |
| 2025-05-13 | European country where the Renaissance started |
| 2025-04-13 | Country that fully encloses two others |
| 2025-03-12 | Country that elected its first female P.M. in 2022 |
| 2025-02-25 | Home to the Amalfi Coast |
| 2025-02-14 | Setting for the films "Life Is Beautiful" and "Call Me By Your Name" |
| 2025-01-24 | One of three countries straddled by Mont Dolent |
| 2024-07-21 | Four-time FIFA World Cup winner |
| 2023-06-04 | Major wine-producing country |
| 2023-05-22 | Country surrounding Vatican City |
| 2022-10-21 | Where the piano was invented |
| 2022-05-04 | Colosseum country |
| 2022-04-02 | Where 23-Down was coined |
| 2020-09-11 | Where eyeglasses and espresso machines were invented |
| 2020-05-31 | Land of the Po (not Poland) |
| 2019-08-19 | See 15-Across |
| 2019-07-04 | Four-time World Cup champion |
| 2019-03-24 | Source of many an imported boot, appropriately |
| 2018-11-19 | Where pasta originated |
| 2018-08-05 | Birthplace of the Renaissance |
| 2018-03-26 | Where the Renaissance began |
| 2014-11-23 | 2006 World Cup winner |
| 2014-06-09 | Rome's home |
| 2014-03-18 | Opera's birthplace |
| 2013-09-13 | Nation with the most Unesco World Heritage Sites |
| 2013-07-31 | An original eurozone member |
| 2011-08-20 | Its calling code is +39 |
| 2011-04-28 | 2006 World Cup champs |
| 2011-01-16 | 2006 World Cup champion |
| 2010-06-24 | "A Farewell to Arms" setting |
| 2010-06-13 | Country with a green, white and red flag |
| 2010-03-03 | Where Orvieto can be found |
| 2010-02-21 | See 2-Down |
| 2010-02-14 | Land of amore |
| 2009-10-12 | Milan's home |
| 2008-04-16 | A G8 nation |
| 2007-04-03 | G8 member |
| 2006-05-05 | Eco location |
| 2005-11-21 | Birthplace of the Renaissance |
| 2005-03-08 | Europe's "boot" |
| 2004-09-07 | "Boot" in the Mediterranean |
| 2003-11-06 | Little ___ |
| 2002-09-09 | Lire used to be spent here |
| 2002-07-14 | World Cup powerhouse |
| 2002-05-23 | *Opera ... wine ... boot |
| 2002-03-13 | Part of a continental tour |
| 2001-10-17 | Peninsular land |
| 2001-10-09 | It surrounds San Marino |
| 2001-08-08 | Leghorn locale |
| 2001-07-24 | Geographical "boot" |
| 2001-04-10 | Where Fiats are made |
| 2001-03-17 | "Enchanted April" setting |
| 2000-10-23 | Milan's land |
| 2000-09-12 | Sicily's "kicker" |
| 2000-08-08 | Where Soave comes from |
| 2000-01-18 | Europe's "boot" |
| 2000-01-01 | "Enchanted April" setting |
| 1999-02-01 | Where Rome is home |
| 1998-04-27 | Little ___ (part of the Big Apple) |
| 1998-02-28 | Taranto's locale |
| 1998-02-23 | Europe's "boot" |
| 1997-01-12 | Autostrada's place |
| 1996-12-22 | Po land |
| 1996-11-12 | "Paradise of exiles": Shelley |
| 1996-02-12 | Country on a continental tour |
| 1995-10-24 | Where Como is |
| 1995-09-03 | Frommer title |
| 1995-05-09 | Land of Milan |
| 1995-04-29 | Leghorn locale |
| 1995-04-10 | Country in a grand tour |
| 1995-03-15 | Shelley's "Paradise of exiles" |
| 1994-10-27 | New York's Little _____ |
| 1994-08-23 | One of 38-Across |
| 1994-04-22 | Three-time World Cup winner |