Born on the 17th April 1961, Raymond was raised and brought up in the town of Saltcoats. He attended Kyleshill Primary, Argyle Primary and then finally Ardrossan Academy.
The Montgomerie family have ran the Victoria Bar in Raise Street since 1965 and Raymond played for the local junior team, Saltcoats Victoria, with the family having an association with the club going back to 1962, indeed, the pub was named after the team. This was to be the start of Raymond's football career with the 'Vics' in 1979 before moving to professional football with Newcastle United in 1980. After a short spell there, he returned to Scotland to Dumbarton Football Club in 1981 and spent the next 7 years there making over 200 appearances.
In 1988 he moved to Kilmarnock Football Club where he spent an amazing 11 years with over 500 appearances. Towards the end of his career Raymond spent a season with Partick Thistle before hanging up his boots in 2000.
Of course Raymond's greatest time as a footballer was with the great Kilmarnock Scottish Cup win in 1997. At odds of 50/1 of winning the cup, they put East Stirling out in the 3rd round beating them 2-0 at home. In the fourth round they knocked out Clyde in an 1-0 away win.
They met Greenock Morton in the quarter finals and won 5-2 away. After a first meeting draw they knocked Dundee United out at Easter Road 1-0 in the semi-final replay. Saturday 24th May 1997 was the big day against Falkirk at Ibrox Park when they picked up the Scottish Cup after a 1-0 win. It was a really great occasion parading the cup through Kilmarnock on an open top bus which was only bettered by bringing the Scottish Cup home to Saltcoats to let all the regulars and locals see it in the Victoria Bar. Raymond also took the cup the his local church St Cuthberts and the local primary school, Caledonia, for all the kids to see it - the delight in their faces was just fantastic to witness.
Raymond is married to Alison, a local physiotherapist, and they have 3 children; Raymond, Jenna and Matthew, who all attend local schools. Raymond adds: "Saltcoats is the place for me because of its people and the way they make everyone welcome to our small town."
