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border (up)on (something)

1. Literally, to be positioned next to something. France borders upon Spain to the south. That shed definitely borders on our property.
2. To be very similar to something without being identical; to nearly be something. Be careful, some sections of this paper are bordering on plagiarism.
See also: border

work both sides of the street

1. Literally, to occupy positions on both sides of a single street in order to sell something to people walking on either side. Our sales were doing OK, but it wasn't until I hired a second food truck and started working both sides of the street that things really took off.
2. To aid, support, or engage with both sides of some issue, situation, agenda, competition, etc. Usually used with the implication of doing so in a duplicitous manner to benefit one's own interests or agenda, though not always. She was accused of working both sides of the street, acting as a legal adviser for groups trying to legalize recreational cannabis while also serving on the board of several organizations that have tried to quash actions. Look, I've been working both sides of the street in Washington for years, negotiating the rather volatile divide between corporate and political interests very carefully.
See also: both, of, side, street, work
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

border (up)on something

 
1. Lit. [for something] to touch upon a boundary. (Upon is more formal and less commonly used than on.) Our property borders on the lakeshore. The farm borders upon the railroad tracks.
2. Fig. [for some activity or idea] to be very similar to something else. (Not usually physical objects. Upon is formal and less commonly used than on.) This notion of yours borders upon mutiny! That plan borders on insanity.
See also: border, on
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.

work both sides of the street

Engage in doubledealing, be duplicitous, as in The real estate agent was known for working both sides of the street, advising first the buyer and then the seller . This metaphoric term transfers opposite sides of a street to opposite sides of a negotiation.
See also: both, of, side, street, work
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

border on

or border upon
v.
1. To be next to something in location: New York State borders on Lake Ontario. My property borders upon a small lake.
2. To come close to being something, especially in association, meaning, or intent; verge on something: Your harsh criticism borders on being offensive. Some of their jokes were funny, but others bordered upon the ridiculous!
See also: border, on
The American Heritage® Dictionary of Phrasal Verbs. Copyright © 2005 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

work both sides of the street

To engage in double-dealing; be duplicitous.
See also: both, of, side, street, work
American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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References in periodicals archive ?
| Duty Nobly Done - The South Wales Borderers at Gallipoli 1915 (RRP PS29.95), by Rodney Ashwood, is available direct from the publishers at www.helion.co.uk as well as from Amazon and other bookshops.
Representatives from the Kings Own Scottish Borderers, South Staffs regiment, Bedworth Paras, Ox and Bucks Light Infantry and the first and sixth airbourne divisions were also at the funeral to say their last goodbyes.
I would like to be able to trace whether grandad was with the King's Own Scottish Borderers or with the International Brigade..
Aled Davies had already notched up 10 points with the boot and, with the last kick of this incredible match, he secured victory for the Borderers with the conversion.
Fred Tattersall took advantage of the government's Heroes Return grants to organise a party of 11 King's Own Scottish Borderers.
Mike Rainey added the conversion but the Borderers hit back with a Scott Ruthven penalty.
I AGREE with W St Clair (Feedback, June 26) that the South Wales Borderers were not mentioned in your article on the presentation of the Colours to the Regiment of Wales.
Troops from the Royal Scots Borderers 1 SCOTS served in Malawi, Kenya, Cyprus, Jordan, Sierra Leone and Bosnia in the last year.
The Borderers snatched three points from Stirling in their last encounter when Lee Currie rifled in a 25-yard free-kick three minutes before the final whistle.
Lord Touhig said: "The film Zulu was re-run on television last weekend telling the story of the South Wales Borderers' defence of the mission station at Rorke's Drift in Natal in a battle with the Zulus in 1879.
Born in Rugby, Mr Adams attended Stoke Secondary School and as a young man joined the King's Own Scottish Borderers.
It was the final goodbye of the Kings Own Scottish Borderers last Tuesday.
Bottom club Fleur-de-Lys put up a good fight against third-placed Whitland and were leading 14-12 at half-time, but the superior strength of the Borderers became apparent in the second half and the visitors ran out 25-17 victors.
Panels of experts at Bangor and Aberystwyth will also debate the merits of the movie, which showed the heroism of a handful of South Wales Borderers who won many Victoria Crosses in the bloody and legendary battle with the Zulus at Rorke's Drift in 1879.
They kept up the momentum to earn their first league triumph over the Borderers for three years.