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Scottish National Dictionary (1700–)

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ROWLIE-POWLIE, n.comb. Also rowley-powley (Rnf. 1827 W. Taylor Poems 12, Abd. 1853 W. Cadenhead Flights 182; Sc. 1887 G. Outram Lyrics 105), rowley-powly (Lnk. 1895 W. Fraser Whaups 11), rowly powl (Edb. 1773 Fergusson Poems (S.T.S.) II. 165), rowly powly (Lnk. 1882 A. Nimmo Songs 195); roulie-poulie (w.Sc. 1880 Jam.); rollie-polie (Ayr. 1913 J. Service Memorables 235). Sc. forms and usages of Eng. roly-poly. [′rʌuli-]

1. As in Eng., a game of chance chiefly consisting in the rolling of a ball to reach a certain spot or knock down certain targets. In Sc. specif. of a form of Kyles or nine-pins, played at fairs with a pole or cudgel and a number of pins (w.Sc. 1880 Jam.), and as in quots. Also attrib.Sc. 1821 Blackwood's Mag. (Nov.) 393:
The players at rowley-powley cleared an avenue for the path of the stick, thrown at pegs topped with penny-cakes of gingerbread.Edb. 1828 D. M. Moir Mansie Wauch xxiii.:
A rowley-powley man . . . to trail about the country frequenting fairs.Rnf.⁴ 1934:
A weaver's pirn, embedded in clay, was set up, with a button on the top, and the participant in the game threw another pirn at the "rowley-powley" in hopes of upsetting it.

2. A fair-ground stall-holder in charge of a game of rollie-poly. Also in reduced form rowley.Lnk. a.1832 W. Watt Poems (1860) 352:
Now mony a scowry prick-the-loop, And ragged rowly-powly.Ags. c.1847 J. McBain Arbroath (1887) 186:
Aft wi' the rowleys did they meet.Ags. 1864 Arbroath Guide (23 July) 3:
And rowly powly cried, 'Come on'.

3. Fig. a risky or doubtful undertaking.Ayr. 1822 Galt Entail xcii.:
I hae a notion to try my luck and fortune in the rowley-powley o' a law-plea.