Kenny - a member of the Glasgow Warriors coaching team - and Caskie � Scotland under-18 assistant coach and director of rugby at Dollar Academy - will spend three weeks in New Zealand�s south island, working with the coaching staff of Super Rugby side Canterbury Crusaders, in their high performance unit in Christchurch.
Kenny, made the switch to the Glasgow Warriors from RBS Premiership team Ayr for the 2013/14 season, after guiding the Millbrae side to two Premiership titles and three RBS Cup wins.
In his inaugural year as assistant coach at Scotstoun, the Warriors have battled their way into the RaboDirect PRO12 final, a first for any Scottish side.
He said: �This is a great opportunity for me to go back to New Zealand, having been a couple of times previously, and really get involved with the Crusaders coaching set-up, especially with the likes of Todd Blackadder.
�Coming into the Warriors� frame last year was a big break, and huge step-up, for me, and this is yet another chance for me to develop myself further in a professional environment.
�A couple of areas that I have outlined as of interest to me include the usual game structure and strategy, as well as absorbing the cultural element of the club and the country.
�England play both the Crusaders and New Zealand when I�m over, so that�s something I would really like to get involved in, to see how the teams prepare on the build-up to their big games.�
Caskie, has had experience on the international rugby stage in a coaching role, as he was part of the Georgia national team during their 2011 Rugby World Cup campaign in New Zealand.
He said: �I�m approaching this experience with two hats on, one being my role with Scotland under-18, and the other my director of rugby position at Dollar Academy.
�This is an opportunity for me to see what other people do, especially in such a rich rugby culture like New Zealand�s, and reflect on how it differs to the way we operate back here in Scotland.
"I�ll be looking to get a taste of everything from under-11 school rugby all the way through to the professional game, and gain an insight into the process put in place to progress talent at each stage of their development.�
The Macphail Scholarship was established in memory of former Scotland hooker John Macphail, who died in 2004. In Macphail's business career, he was chief executive then chairman, of the Edrington Group, a private company that is owned by the Robertson Trust. Macphail was a trustee of the Robertson Trust for 28 years and chairman for 19 of those years.
Previous coaching recipients of the Macphail Scholarship include Shade Munro, Chris Paterson, Iain Monaghan, Ben Fisher and Alex Duncan.
Kenneth Ferguson, Director of The Robertson Scholarship Trust, said: �We are delighted to give these two highly experienced coaches the chance to travel to New Zealand as the winners of this year�s John Macphail Scholarship.
�We hope that the experience will help both recipients grow in their already successful careers, and allow them to share the experience with those they coach now, and in the future.
�Along with the Trustees and the Macphail family, we look forward to following the progress of Kenny and Don, both in New Zealand and in their subsequent careers.�