| Overseer, usually hard | 22 |
| Overseers | 9 |
| Overseers of a sort | 19 |
| Overseers of monk-y business? | 29 |
| Overseers: Abbr. | 16 |
| Oversees | 8 |
| Oversees productions | 20 |
| Oversees, with "on" | 29 |
| Oversell | 8 |
| Oversensitive | 13 |
| Oversensitiveness | 17 |
| Oversentimental | 15 |
| Oversentimental journalist | 26 |
| Oversentimentality | 18 |
| Overshadow | 10 |
| Overshadowed | 12 |
| Overshadowed, with "above" | 36 |
| Overshadows | 11 |
| Overshoe | 8 |
| Overshoe cord | 13 |
| Overshoes for the pursuer | 25 |
| Overshoot | 9 |
| Overshoot, say | 14 |
| Overshoots the puck | 19 |
| Overshot | 8 |
| Overshot exit ramp in Dallas's sister city? | 47 |
| Oversight | 9 |
| Oversight cause, maybe | 22 |
| Oversights | 10 |
| Oversimplifies, as educational standards | 40 |
| Oversimplify | 12 |
| Oversimplify, with "down" | 35 |
| Oversize coif | 13 |
| Oversize envelope | 17 |
| Oversize hairdos | 16 |
| Oversize reference book | 23 |
| Oversize sunglasses, these days | 31 |
| Oversize volume | 15 |
| Oversize wine bottle | 20 |
| Oversize, as a map | 18 |
| Oversize-load escort vehicle | 28 |
| Oversized | 9 |
| Oversized audio component? | 26 |
| Oversized beer can | 18 |
| Oversized beer serving? | 23 |
| Oversized chocolate chip | 24 |
| Oversized cleaning tool? | 24 |
| Oversized drink name | 20 |
| Oversized European import? | 26 |
| Oversized hairdo | 16 |
| Oversized library volume | 24 |
| Oversized meals for Fred Flintstone, maybe? | 43 |
| Oversized piece of jewelry? | 27 |
| Oversized reference book | 24 |
| Oversized sailing vessel? | 25 |
| Oversized Scrabble squares on which to play vowels? | 51 |
| Oversized semi | 14 |
| Oversized spoon | 15 |
| Oversized volume | 16 |
| Oversized volume, often | 23 |
| Oversized volumes | 17 |
| Oversleeper | 11 |
| Oversleeper's need | 22 |
| Overspread | 10 |
| Overspreads | 11 |
| Overstarched collar problem | 27 |
| Overstate | 9 |
| Overstate one's case | 24 |
| Overstay one's welcome at the podium | 40 |
| Overstay one's welcome, e.g. | 32 |
| Overstays? | 10 |
| Overstep | 8 |
| Overstep a boundary | 19 |
| Overstep the line? | 18 |
| Overstepping a rule | 19 |
| Oversteps one's bounds | 26 |
| Overstock | 9 |
| Overstretch | 11 |
| Overstrung | 10 |
| Overstudious one | 16 |
| Overstudious sort | 17 |
| Overstudious students | 21 |
| Overstuff | 9 |
| Overstuffed | 11 |
| Overstuffed footstool | 21 |
| Overstuffed furniture? | 22 |
| Overstuffed piece | 17 |
| Overstuffed with dialogue | 25 |
| Overstuffed with dialogue, as some films | 40 |
| Overstuffing | 12 |
| Overstuffs | 10 |
| Oversupplies | 12 |
| Oversupply | 10 |
| Oversupply a market | 19 |
| Oversweet substance | 19 |
| Overt | 5 |
| Overt play for sympathy? | 24 |
| Overtake | 8 |
| Overtake and attack, oater style | 32 |
| Overtake and go beyond | 22 |