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| 2008.09.24 | Wednesday | home | Chester 1 | lost | 1½-3½ |
| 2008.09.30 | Tuesday | away | Chester 2 | won | 4-1 |
| 2008.10.15 | Wednesday | home | Wrexham | lost | 1-4 |
| 2008.11.05 | Wednesday | home | Colwyn Bay | won | 3½-1½ |
| 2008.11.18 | Tuesday | away | Rhyl | won | 3-2 |
| 2008.12.08 | Monday | away | Holywell | lost | 1-4 |
| 2009.01.13 | Tuesday | away | Chester 1 | won | 3-2 |
| 2009.01.21 | Wednesday | home | Chester 2 | won | 3-2 |
| 2009.02.24 | Tuesday | away | Wrexham | lost | 1½-3½ |
| 2009.03.17 | Tuesday | away | Colwyn Bay | lost | 1½-3½ |
| 2009.03.25 | Wednesday | home | Rhyl | won | 3½-1½ |
| 2009.04.08 | Wednesday | home | Holywell | won | 4½-½ |
| Chester League Division 1 | P | W | D | L | F | A | P |
|---|---|---|---|---|---|---|---|
| Wrexham | 12 | 12 | 0 | 0 | 46 | 14 | 12 |
| Chester 1 | 12 | 9 | 0 | 3 | 37½ | 22½ | 9 |
| Colwyn Bay | 12 | 7 | 0 | 5 | 33 | 27 | 7 |
| Caergwrle | 12 | 7 | 0 | 5 | 31 | 29 | 7 |
| Rhyl | 12 | 3 | 1 | 8 | 24½ | 35½ | 3½ |
| Holywell | 12 | 2 | 2 | 8 | 22½ | 37½ | 3 |
| Chester 2 | 12 | 0 | 1 | 11 | 15½ | 44½ | ½ |
| David | Bennion | ½-½ | Haydn | Parry |
| John | Gorman | 1-0 | Liam | Jefferies |
| Edwin | Livesey | 1-0 | Max | Coventry |
| Neville | Layhe | 1-0 | H | Roberts |
| David | Parker-Williams | 1-0 | B | Hird |
Caergwrle 1 finished the season with a record win. Dave Parker-Williams won a piece off his opponent, and Edwin Livesey and Neville Layhe also won material. Caergwrle went 4-0 up after John Gorman, Edwin Livesey, Neville Layhe and Dave Parker-Williams won their games. Dave Bennion was playing in the last game to finish, it was agreed a draw after an even game. This was a record win for Caergwrle 1 in the Chester first division, we have yet to win 5-0.
CAERGWRLE WON 4½-½| Robert | Clark | ½-½ | Les | Simcock |
| David | Bennion | 1-0 | Michael | Williams |
| John | Gorman | 1-0 | Chris | Grier |
| Graham | Williams | 0-1 | Andrew | Nicol |
| David | Dickson | 1-0 | John | Simmons |
Dave Dickson was making an appearence for the first team and won on bottom board against league president John Simmons. After Bob Clark drew his game and Graham Williams lost his the score was 1½ each with Dave Bennion and John Gorman still playing. Dave Bennion mated his opponent in a double rook ending, and John Gorman's opponent Chris Grier ran out of time.
CAERGWRLE WON 3½-1½| David | Jameson | ½-½ | Robert | Clark |
| John | Blore | 0-1 | David | Bennion |
| Richard | Burton | 1-0 | David | Parker-Williams |
| Michael | Whale | 1-0 | Graham | Williams |
| Brendon | Shields | 1-0 | Michael | Friel |
Caergwrle are unable to win the league and John Gorman and Edwin Livesey were unavailable. Caergwrle were beaten on the bottom boards in this match, Mike Friel and Graham Williams lost on the bottom two boards. Dave Bennion won aginst Chester league individual champion John Blore and Bob Clark drew against Dave Jameson. This left Caergwrle a point down, Dave Parker-Williams neading a win to draw the match. Dave was always losing in a queen ending, and with his flag about to fall he resigned his game.
CAERGWRLE LOST 1½-3½| Charles | Morris | 1-0 | David | Bennion |
| David | James | ½-½ | John | Gorman |
| Ray | Holland | 0-1 | Edwin | Livesey |
| David | Simpson | 1-0 | David | Parker-Williams |
| Brian | Davies | 1-0 | David | Dickson |
Dave Bennion and Dave Dickson lost their gasmes in this match. Dave Parker-Williams made it a full set of losses for the Daves when he lost to David Simpson. Dave had played well but went to pieces in the ending and resigned in a drawn position. Edwin Livesey won after sacrificing his queen against Ray Holland, John Gorman was winning in an ending against Dave James but could only draw.
CAERGWRLE LOST 1½-3½| David | Bennion | 1-0 | Debidulay | Nunes |
| John | Gorman | ½-½ | Steven | Lloyd |
| Robert | Skinner | 0-1 | John | Sutcliffe |
| Edwin | Livesey | 1-0 | Paul | Harnett |
| David | Parker-Williams | ½-½ | Harry | Bullard |
Bob Clark was missing for this game and Caergwrle struggled to win against the bottom of the table side. Dave Bennion sacrificed in his game and won on top board, whilst Edwin Livesey was losing, but won in the end. John Gorman and Dave Parker-Williams drew their games whilst Rob Skinner lost against ex-Caergwrle John Sutcliffe.
CAERGWRLE WON 3-2| Chris | Doran | ½-½ | David | Bennion |
| Paul | Watson | 0-1 | Robert | Clark |
| David | Bryan | ½-½ | John | Gorman |
| Graham | Bromley | 0-1 | Robert | Skinner |
| Joe | Nemcek | 1-0 | Michael | Friel |
Caergwrle defeated Chester 1 in a close match, Bob Clark and Rob Skinner had good wins. Mike Friel lost on bottom board, whilst John Gorman drew his game. Dave Bennion seemed to be winning his game but could only draw in the end.
CAERGWRLE WON 3-2| Haydn | Parry | ½-½ | John | Gorman |
| Liam | Jefferies | ½-½ | Graham | Williams |
| Max | Coventry | 1-0 | David | Dickson |
| Terry | Scott | 1-0 | Michael | Friel |
| Default | won | 1-0 | Default |
Dave Bennion and Bob Clark were missing for Caergwrle as were others and so Caergwrle were a player short. It was a bad evening with no wins, Graham Williams was made inelligible for the second after playing on board two but he drew his game.
CAERGWRLE LOST 1-4| Les | Simcock | ½-½ | Robert | Clark |
| Michael | Williams | 0-1 | David | Bennion |
| Chris | Grier | ½-½ | John | Gorman |
| John | Simmons | 0-1 | Edwin | Livesey |
| Ian | Lloyd | 1-0 | Robert | Skinner |
This was an easy match on paper for Caergwrle but Ian Lloyd had not been reading the script when he won on bottom board for Rhyl. After Dave Bennion and Edwin Livesey had won and Bob Clark had drawn, the score was 2½-1½ to Caergwrle. John Gorman needed a draw to win the match against Chris Grier. It seemed that John might lose but it ended in a draw.
CAERGWRLE WON 3-2| Robert | Clark | 1-0 | David | Jameson |
| David | Bennion | ½-½ | John | Blore |
| John | Gorman | 1-0 | Richard | Burton |
| Edwin | Livesey | 1-0 | Jack | Taylor |
| David | Parker-Williams | 0-1 | Michael | Whale |
Bob Clark won well on top board against Dave Jameson, whilst John Gorman and Edwin Livesey won their games. Dave Bennion was a piece up in his game, but was losing pawns, the game was agreed a draw in the ending, David Parker-Williams lost to Mike Whale.
CAERGWRLE WON 3½-1½| Robert | Clark | 0-1 | Richard | Dineley |
| David | Bennion | ½-½ | Charles | Morris |
| John | Gorman | 0-1 | David | James |
| Edwin | Livesey | 0-1 | David | Simpson |
| Robert | Skinner | ½-½ | Brian | Davies |
Wrexham had three Welsh internationals playing on the top three boards, and they also play for the South Wales Dragons in the national league, With Dave Bennion there were four SW Dragons players playing. Caergwrle could only get two draws in this match, with Bob Clark losing to Richard Dineley in a rook ending, and John Gorman and Edwin Livesey also losing. Dave Bennion was a pawn up but eventually got a draw in a rook ending while Rob Skinner got a draw with Brian Davies.
CAERGWRLE LOST 1-4| Steven | Lloyd | 0-1 | Robert | Clark |
| Paul | Harnett | 0-1 | David | Bennion |
| John | Sutcliffe | 0-1 | John | Gorman |
| David | Hulme | 0-1 | Edwin | Livesey |
| Colin | White | 1-0 | David | Parker-Williams |
Caergwrle first team got their first win of the season against Chester 2. Bob Clark won his game while David Parker-Williams lost, making the score 1-1. Dave Bennion and John Gorman's opponents resigned as they were about to get mated, Edwin Livesey won in the ending.
CAERGWRLE WON 4-1| Robert | Clark | 0-1 | Chris | Doran |
| David | Bennion | ½-½ | Mathew | Demmon |
| John | Gorman | 1-0 | Paul | Watson |
| Edwin | Livesey | 0-1 | Richard | Bryant |
| David | Parker-Williams | 0-1 | Graham | Bromley |
Caergwrle first team lost the first match of the season against a strong Chester 1 side. It was the first defeat since 2007.04.04 when they lost to Chester 2. David Parker-Williams was a piece up but blundered badly and lost, while Bob Clark lost in an ending to Chris Doran. Dave Bennion was losing in a rook ending but salvaged a draw, Edwin Livesey lost but John Gorman won the remaining game on time against Paul Watson.
CAERGWRLE LOST 1½-3½| Charles | Morris | 1-0 | David | Bennion |
| Ray | Holland | ½-½ | Robert | Clark |
| David | Simpson | 1-0 | John | Gorman |
| John | Canham | 0-1 | Edwin | Livesey |
| Brian | Davies | 1-0 | Graham | Williams |
| Peter | Fisher | 1-0 | Michael | Friel |
Edwin Livesey was the only winner for Caergwrle, beating the experienced John Canham. Bob Clark seemed to winning against Ray Holland but drew in the end. Pete Fisher had a good win for Wrexham on bottom board.
CAERGWRLE LOST 1½-4½| David | Bennion | 1-0 | David | Castledine |
| Robert | Clark | 1-0 | D | Evans |
| John | Gorman | 1-0 | Joe | Ventre |
| Edwin | Livesey | 1-0 | Frank | Davies |
| Robert | Skinner | 1-0 | Gerald | Solomon |
| David | Parker-Williams | 1-0 | Andrew | Ballard |
Corwen had a three and a half point start in this match, which is the handicap for a first division team against a third division team. Bob Clark struggled a bit but won his game, Dave Parker-Williams, Rob Skinner Edwin Livesey and John Gorman also won their games. On top board Dave Bennion won in the ending against Dave Castledine.
CAERGWRLE WON 6-3½| 2008.09.16 | Tuesday | away | Chester 3 | lost | 1-4 |
| 2008.10.01 | Wednesday | home | Frodsham | lost | 1-4 |
| 2008.10.06 | Monday | away | Capenhurst | lost | 1-4 |
| 2008.10.22 | Wednesday | home | Rhyl 2 | won | 3-2 |
| 2008.11.24 | Monday | away | Buckley-Mold 1 | lost | 1½-3½ |
| 2008.12.03 | Wednesday | home | Colwyn Bay & Llandudno 2 | lost | 1-4 |
| 2009.01.19 | Monday | away | Frodsham | lost | 1-4 |
| 2009.02.18 | Wednesday | home | Capenhurst | draw | 2½-2½ |
| 2009.03.03 | Tuesday | away | Rhyl 2 | won | 3-2 |
| 2009.03.25 | Wednesday | home | Buckley-Mold 1 | won | 3-2 |
| 2009.04.14 | Tuesday | away | Colwyn Bay & Llandudno 2 | lost | 0-5 |
| 2009.04.22 | Wednesday | home | Chester 3 | lost | 0-5 |
2009.03.25 The second team defeated Buckley-Mold first team 3-2, there was a good win for Wolfgang Lenze against Jim Hanson who has scored a lot of points in the lower divisions.
2008.10.22 Caergwrle second team put an end to the run of losses, with a 3-2 win against Rhyl 2. The match had been 2-2 Mike Friel winning the final game for a 3-2 win.
2008.10.06 Caergwrle second team have begun the season with three 4-1 losses, the latest was against Capenhurst. The one point was a default, as Capenhurst were a player short.
2008.10.01 Caergwrle second team lost 4-1 at home to Frodsham, Dave Dickson was the only winner.
2008.09.16 Caergwrle second team lost 4-1 to Chester third team, Mike Friel was the only winner, so it has been a bad start to the season for Caergwrle.
| Final | 2009.05.07 | Thursday | away | Wallasey | lost | 3-4 |
| Semi-Final | 2009.03.11 | Wednesday | home | Hoylake | won | 5½-1½ |
| Quarter-Final | 2008.10.15 | Wednesday | home | Buckley-Mold | won | 6-3½ |
| 2008.10.10 | Friday | away | Pensby | won | 5-0 |
| 2008.11.26 | Wednesday | home | Chester 1 | draw | 2½-2½ |
| 2008.12.15 | Monday | away at Wallasey | Formby | won | 3½-1½ |
| 2009.01.06 | Tuesday | away | Hoylake 1 | won | 3½-1½ |
| 2009.02.18 | Wednesday | home | Wallasey 1 | won | 5-0 conceded |
| 2009.03.04 | Wednesday | home | Chester 2 | won | 4½-½ |
| 2009.03.05 | Thursday | away | Wallasey 2 | won | 4½-½ |
| 2009.04.01 | Wednesday | home | Wallasey 3 | won | 3-2 |
| 2008.09.10 | Wednesday | home | Wrexham | lost | 2-3 |
| 2008.10.15 | Wednesday | home | Buckley-Mold 1 | won | 3-2 |
| 2008.10.28 | Tuesday | away | Chester 3 | ||
| 2008.11.17 | Monday | away | Wallasey 4 | lost | |
| 2009.01.07 | Wednesday | away | Buckley-Mold 2 | won | 3-2 |
| 2009.03.18 | Wednesday | home | Wallasey 5 | won | 5-0 |
| 2009.04.27 | Monday | away | Capenhurst | lost | ½-4½ |