| ___ Sad (Serbian city) | 22 |
| ___ Sad (Serbia's second-largest city) | 42 |
| ___ Sad (city on the Danube) | 28 |
| ___ Sad (capital of Vojvodina) | 30 |
| ___ Sack (kickable beanbag) | 27 |
| ___ sack | 8 |
| ___ sac (pouch between bones and tendons) | 41 |
| ___ Sabha, India's lower house | 34 |
| ___ Sabha (Indian legislature) | 30 |
| ___ Sabe (trusty scout) | 23 |
| ___ sabe (Tonto's friend) | 29 |
| ___ Sabe (Lone Ranger) | 22 |
| ___ sabe (friend, to Tonto) | 27 |
| ___ sabe | 8 |
| ___ sabaki (martial arts movement) | 34 |
| ___ Saab (French fashion designer) | 34 |
| ___ S. Cobb | 11 |
| ___ Ryerson in "Groundhog Day" | 40 |
| ___ rye (deli order) | 20 |
| ___ rye (deli offering) | 23 |
| ___ Ryan, a k a the Ryan Express | 32 |
| ___ Ruxpin (toy bear) | 21 |
| ___ Rutherford, the Father of Nuclear Physics | 45 |
| ___ Ruth | 8 |
| ___ rut | 7 |
| ___ Russian | 11 |
| ___ Russia (title of Ivan IV) | 29 |
| ___ Rushmore | 12 |
| ___ rush | 8 |
| ___ running | 11 |
| ___ run of bad luck | 19 |
| ___ run average | 15 |
| ___ run (cross the plate) | 25 |
| ___ run (baseball move) | 23 |
| ___ run | 7 |
| ___ rummy | 9 |
| ___ rum | 7 |
| ___ Ruler, Secretariat's sire | 33 |
| ___ rule, at a convention | 25 |
| ___ rule (usually) | 18 |
| ___ rule (ordinarily) | 21 |
| ___ rule (normally) | 19 |
| ___ rule (generally) | 20 |
| ___ rule | 8 |
| ___ Ruins National Monument, N.M. | 33 |
| ___ rug (small floor covering) | 30 |
| ___ rug (jitterbugs) | 20 |
| ___ rug (dance) | 15 |
| ___ rug (cavort) | 16 |
| ___ rug | 7 |
| ___ Ruess, lead singer of Fun | 29 |
| ___ Rud, river on Afghanistan's boundary | 44 |
| ___ Rud, river in Iran | 22 |
| ___ Rud river | 13 |
| ___ Rubik, inventor of a cube | 29 |
| ___ Rubik, cube man | 19 |
| ___ Rubik, cube inventor | 24 |
| ___ Rubik (cube inventor) | 25 |
| ___ Rubicon (commit oneself) | 28 |
| ___ rubber (shoe material) | 26 |
| ___ rubber | 10 |
| ___ rub | 7 |
| ___ Royce, disco group | 22 |
| ___ Royale, N.S. | 16 |
| ___ Royale, Mich. | 17 |
| ___ Royale Park | 15 |
| ___ Royale National Park | 24 |
| ___ Royale (Lake Superior park) | 31 |
| ___ Royale (Lake Superior feature) | 34 |
| ___ Royale (Depression-era car) | 31 |
| ___ Royale (cocktail) | 21 |
| ___ Royale | 10 |
| ___ Royal, W.W. II aircraft carrier | 35 |
| ___ Royal, Quebec | 17 |
| ___ royal, highest rear deck | 28 |
| ___ Royal Majesty | 17 |
| ___ Royal Highness | 18 |
| ___ Royal (Louvre neighbor) | 27 |
| ___ Roy (Scottish hero) | 23 |
| ___ Roy | 7 |
| ___ Row (bespoke tailoring locale) | 34 |
| ___ Row | 7 |
| ___ rover (children's game) | 31 |
| ___ rover | 9 |
| ___ route (pitch nine innings) | 30 |
| ___ rouser | 10 |
| ___ Round Table (erstwhile New York City intelligentsia collective) | 67 |
| ___ Rouge, Paris | 16 |
| ___ Rouge, La. | 14 |
| ___ Rouge, Cambodian guerrilla | 30 |
| ___ Rouge (Red Mill) | 20 |
| ___ Rouge | 9 |
| ___ Rote of football fame | 25 |
| ___ rotation | 12 |
| ___ roster (eligible team members) | 34 |
| ___ Ross, author of "Wisconsin" | 41 |
| ___ Ross Bridge (Delaware crosser) | 34 |
| ___ Rosita, city in Mexico | 26 |
| ___ Roses (band that returned with a 2008 album) | 48 |
| ___ roses | 9 |