In the 2007-2008 season Caergwrle won the Chester league title, for the first time in their history. The handicap knockout was won in 2002 wnen we played in the second division. In the 1997-1998 season Caergwrle won the third division title, so the second division is the only thing we have not won.
| Robert Clark | 1999-2000 | Division 1 |
| David Jameson | 1999-2000 | Division 3 |
| David Jameson | 2000-2001 | Division 3 |
| Michael Driscoll | 2001-2002 | Division 3 |
| David Jameson | 2004-2005 | Division 2 |
| David Bennion | 2006-2007 | Division 1 |
| David Bennion | 2007-2008 | Division 1 |
The player of the season is the league top scorer. In the 1999-2000 Bob Clark was the division 1 top scorer, though he was a Chester player at the time, he joined Caergwrle at the beginning of the 2007-2008 season. Mike Driscoll used to play for Caergwrle in the Wirral league, he was a Ruthin player when he was top scorer in division three in the 2001-2002 season. David Jameson also plays for Caergwrle in the Wirral league, as a Colwyn Bay player he was top scorer in division three in 1999-2000 and 2000-2001, in the 2004-2005 season he was division 2 top scorer. Dave Bennion was division 1 top scorer in 2006-2007 and 2007-2008.
Apart from the player of the season there is also the league individual championship, usually played in November. In the twenty-first century David Jameson and Haydn Parry have been league champions, Dave in 2000, 2001 and 2006, and Haydn in 2005. Both are Wirral league players, Dave plays for Colwyn Bay & Llandudno in the Chester league and Haydn for Holywell after leaving Buckley-Mold. In the previous century Dave Bennion, John Gorman and Bob Clark have been league champions. John Canham has also played for Caergwrle, I believe he has also been league champion, but do not quote me on that.
There have been a few close shaves in the Wirral league, in the 2007-2008 season Caergwrle finished one point off the top. We played Chester in the final of the 2006-2007 knockout final which was a 3½-3½ draw. Chester won on board count or in other words they won on the higher boards. There was one year when we almost won the league title, it all rested on an adjudication which went against us. Dave Jameson was division 1 top scorer in the 2006-2007 season, and Edwin Livesey was the second division top scorer in 2007-2008.
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