The JENNINGS CUP was instigated by the respective club Presidents (Bob Keegan Sorrento & Clarrie Jennings Rye) and was first contested in 1970 as the Bob Keegan Shield and in the late 80s became the Jennings Cup. The annual contest between the two clubs has always been a spirited affair.

Clarrie Jennings played football with the Sorrento FC in 1936, where his playing record was interrupted by his war service during WWII, he returned to Sorrento in 1946 and in that year he won their Most Consistent Trophy. Clarrie played a total of 66 senior games during his time at Sorrento.

In 1947, Clarrie started his dynasty at the Rye FC he was appointed Captain/Coach in 47, winning that years B&F and leading the club into the 47 Grand Final in only the clubs second year. He continued as CC in 48, 49, 50 and 53, along the way winning a Premiership flag in 1951 also winning the B&F that year. During those years the club never finished lower than third! His vigorous tear-through style at center half back earned him the nickname bowler. Clarrie finished his playing career in 1956 amassing 202 games.

In 1959 he was appointed the clubs second President a position that he held for a record 21 years during Clarries time as President the club played in 15 finals series, winning senior premierships in 59, 64, 65 and 72.

His four sons Mick, Dan, Paul & David, as well as his grandsons Chris, Kyle & Aaron all played senior football with Rye. Chris followed in his grandfathers footsteps in playing for both Rye & Sorrento.

Dan Jennings played 9 AFL games with Melbourne, was a member of the Rye FC 72 Senior Premiership team, senior CC in 73, 74, won the senior B&F in 76 and was a member of the Reserves Premiership teams of 65 and 81. He played 252 games for our club.

Dans son, Kyle,  has  played 175 games. He captained the 2007 Reserves Premiership team, and was playing Coach of the Reserve team that won another Premiership in 2009. Kyle is also the third generation of Jennings to serve on the Rye FC committee.

Clarries contribution to the Rye FC was immeasurable, and his memory lives on through the Jennings name on the field. The winner of the Jennings Cup today will know that they will hold a piece of silverware that has been fought for by many, many players from both sides over the past 38 years.