| Old head of state | 17 |
| Old headstones | 14 |
| Old headwear for women | 22 |
| Old health resorts | 18 |
| Old heap | 8 |
| Old heartthrob Flynn | 20 |
| Old heaters | 11 |
| Old heavyweight champ Willard | 29 |
| Old Hebrew avenger | 18 |
| Old Hebrew liquid measure | 25 |
| Old Hebrew measure | 18 |
| Old Hebrew measures | 19 |
| Old hi-fi recordings | 20 |
| Old hi-fi records | 17 |
| Old hi-fis | 10 |
| Old Hickory carried one | 23 |
| Old Highlands dagger | 20 |
| Old highway name | 16 |
| Old highway to Fairbanks | 24 |
| Old highways in Britain | 23 |
| Old Hindu funeral tradition | 27 |
| Old Hindu language | 18 |
| Old hippie hangout, with "the" | 40 |
| Old hippie who plays an even older hippie in "Wanderlust" | 67 |
| Old hit TV show set in Korea | 28 |
| Old hockey nickname | 19 |
| Old holder of writing fluid | 27 |
| Old Hollywood initials | 22 |
| Old Hollywood low-budget studios, collectively | 46 |
| Old Hollywood star with a mustache | 34 |
| Old Hollywood's Dunne | 25 |
| Old Hollywood's method of promoting talent | 46 |
| Old home computer brand | 23 |
| Old home decorations | 20 |
| Old home for Mr. Met | 20 |
| Old home loan org. | 18 |
| Old home owner, often | 21 |
| Old homesteads | 14 |
| Old Honda sports car | 20 |
| Old hook-shaped ski lift | 24 |
| Old hoops gp. | 13 |
| Old hoops grp. | 14 |
| Old hoops org. | 14 |
| Old Horn & Hardart eatery | 29 |
| Old horror flick star Chaney | 28 |
| Old horror star Chaney | 22 |
| Old horror-flick star Chaney | 28 |
| Old horse | 9 |
| Old horse or ex-wife? | 21 |
| Old horse traders? | 18 |
| Old horses | 10 |
| Old horses' home | 20 |
| Old hosiery | 11 |
| Old hospital administration | 27 |
| Old hospital supply | 19 |
| Old Houston gridder | 19 |
| Old Houston hockey team | 23 |
| Old Houston pro | 15 |
| Old Hudson auto | 15 |
| Old hull caulking | 17 |
| Old humor magazine | 18 |
| Old humorist ___ Burgess | 24 |
| Old hunting dog | 15 |
| Old hwy. from Detroit to Seattle | 32 |
| Old hymn, "Te ___" | 28 |
| Old Iberian kingdom | 19 |
| Old IBM computers | 17 |
| Old IBM models | 14 |
| Old IBM offering | 16 |
| Old IBM PC's | 16 |
| Old IBM PCs | 11 |
| Old IBM products | 16 |
| Old ice cream slogan, to ancient Romans | 39 |
| Old Icelandic literary collection | 33 |
| Old Icelandic literary work | 27 |
| Old Icelandic literature | 24 |
| Old Icelandic poems | 19 |
| Old Icelandic poetry | 20 |
| Old Icelandic saga | 18 |
| Old Icelandic work | 18 |
| Old Icelandic writings | 22 |
| Old ideological rival | 21 |
| Old imperator | 13 |
| Old import tax | 14 |
| Old incarnations | 16 |
| Old Indian coins | 16 |
| Old Indian culture of Southwest | 31 |
| Old Indian dominion | 19 |
| Old Indian honorific | 20 |
| Old Indian infantryman | 22 |
| Old Indian leader | 17 |
| Old Indian rule | 15 |
| Old Indian ruler | 16 |
| Old Indian term of respect | 26 |
| Old Indian V.I.P. | 17 |
| Old Indian weight | 17 |
| Old Indianapolis-based automaker | 32 |
| Old Indic dialect | 17 |
| Old Indic lang. | 15 |
| Old Indochina area | 18 |