This month's Cup Match represents some significant milestones in the history of the Classic. Not only will this be the 110th match but this is also the 50th anniversary of one of the biggest individual scores in Cup Match, the 40th year since turf wicket was played on for the first time, 30 years already since arguably the greatest bowler in Cup Match bowled his 599th and final over in the event and 10 years already since Janeiro Tucker scored the highest total by a batsman (186) in the 2001 match at Wellington Oval.In between there has been plenty of drama both on and off the field as often it became downright political on team selection night at both clubs.Cup Match moved into a new era in 1971 when challengers Somerset broke new ground by introducing Cup Match to a turf wicket, still something of a novelty in Bermuda 40 years ago as most clubs were still playing cricket on concrete and matting at the time, matting that they used to carry out onto the middle and secure with string and nails. In 41 matches on turf there have been 27 draws and only 14 victories. In the last 11 years there have been four wins, two by Somerset in 2000 and 2002 and two by St George's in 2005 and 2006.The first century on turf wicket was scored in that first year in ‘71, fittingly that it would be by Somerset's Sheridan Raynor who would go on to become one of the Island's most skilled groundsmen after his playing days.That Cup Match, which ended in a tame draw after Somerset posted 334-8 and then restricted St George's to 244 for a lead of 90 which they extended to 245 before declaring again at 165-2. St George's never took up the challenge but a new star was born on that second day when Noel Gibbons, a 16-year-old colt, scored 67 in an opening stand of 102 with Dennis Wainwright. Lionel Thomas was also a colt for St George's that year.Raynor, who scored 740 runs in his 20-year career, would play only two more Cup Matches before the West Enders duly dropped him in 1974. His brother, Lee, a St George's allrounder, carried the flag for the Raynor family that year by scoring 100 not out at Somerset. Rupert Scotland hit a career-best 120 not out out of a St George's total of 360 for five. Somerset replied with a 96 from Colin Blades his highest in Cup Match and further half centuries from openers Kenny Cann and Campbell Simons, Wendell Simmons and Bergon Spencer in their first innings total of 529. Neither team batted in the second innings.It was the last appearance in Cup Match for big Lloyd James who forced himself into the record books with knocks of 157 in 1961 and a then record 173 not out in 1962. When he retired James was just 12 run short of 1,000 runs in Cup Match, but he resisted the temptation to come out of retirement to reach the milestone.After draws in the first four years on turf wicket (along with the last two on matting in '69 and '70), a victory finally came in 1975 at Somerset when St George's defeated Somerset by 85 runs.The year 1976 marked the arrival of another player who would go on to prominence in Cup Match teenager Wendell Smith of St George's. Gregory Foggo was a colt that year, too, replacing teenager Anthony Trott who made his own debut in the winning team the year before. Randy Raynor, a pace bowler from Southampton Rangers and spinner James Swan were the Somerset colts.Despite Parfitt's heroics the first bowler to take nine wickets in an innings after his 9-47 in Somerset's first innings the match finished in another draw.The same happened in '77 at Wellington Oval where Lionel Thomas nearly broke Lloyd James' individual record blasting 154 out of 222 in the St George's second innings. Eldon Raynor (24) was the only other batsman in double figures.That would prove to be the last year for another St George's stalwart, wicketkeeper Dennis Wainwright, who made way for Allan Douglas, a colt in 1978 along with Arnold Manders and Allen Richardson who opened with Wendell Smith and scored 47 and 40.A bowling milestone was reached in '88 when Clarence Parfitt became the top wicket-taker in Cup Match history, the second behind Alec (Cocky) Steede to take 100 wickets. He went into the match needing four wickets to break Steede's record of 100 wickets and achieved it in spectacular fashion on the first day with figures of 7-18 from 22.5 overs to dismiss Somerset for just 104. For good measure the great man followed up with 5-82 from 40 overs in the second innings.After 20 years without a win the West Enders finally achieved one in 1979 with a victory that will long live in the memory. Many in Somerset will say that the match was won even before the first ball was bowled, as the challengers took a distinct advantage by fielding eight members of the ICC Trophy team that competed in England weeks earlier.St George's, on the other hand, dropped a bombshell by leaving out captain Neville Darrell and replacing him with Gregory (Brutus) Foggo (grandfather of current captain Oronde Bascome) who returned to lead the team in only his second Cup Match. Eldon Raynor was the last of the veterans from the 1960s as Rupert Scotland was also moved out to make way for the recalled Clevie Wade while Clarence Parfitt was abroad playing professionally in Scotland. Clearly the St George's selectors underestimated the superior strength of a determined Somerset team led by cricketer-turned-commentator-turned-politician Randy Horton. Quinton Sherlock, Robert Hinds and ICC Trophy team members Gladstone Brown, Winston Reid, Winston Trott, John Tucker, Joe Bailey, El James, Barry DeCouto and the recalled Colin Blades gave Somerset a clear advantage in the experience department.They made that advantage count as St George's were dismissed for 200 and 73 after Somerset first posted 272-4 on the strength of John Tucker's best Cup Match knock of 84 not out, before declaring again in their second innings on 142-8 on their way to a 141-run victory after Winston (Coe) Trott ripped through St George's with figures of 5-25 in the second innings. A lot of tears were shed by St Georgians that day, many seeing their team lose in Cup Match for the first time.That year spelled the end of the longest-serving player in 1979, Eldon Raynor, a genuine allrounder who could turn a match with his batting, spin bowling or fielding at cover point. He was struck in the head by Robert Hinds while batting and was taken to hospital.“It (injury) was unfortunate but I think that was the turning point in the game,” John Tucker told The Royal Gazette after the match.Between 1958 and '79 Raynor scored 738 runs from 29 innings and also claimed 33 wickets, including 7-18 in 1967, still the seventh best bowling figures in Cup Match.After the '79 loss to Somerset, all eyes were on St George's the following year at Wellington Oval. The challengers made four changes from the previous year as captain Gregory Foggo was dropped and Neville Darrell recalled while Parfitt also returned and was named vice captain. Teenagers Ken Pitcher and Charlie Marshall were the two colts.Just a year earlier Marshall, after leading Bermuda's youth team to the International Youth Tournament title in Canada, spoke of his desire to play for Somerset in Cup Match. Randy Horton urged him to be patient as he was still young and the next year 19-year-old Marshall made the switch to the East End.Somerset made just one change to their winning team, bringing in 21-year-old Ricky Hill as wicketkeeper (after his 53 in the final trial) in place of Quinton Sherlock.Marshall justified the faith St George's showed in him by doing something no other colt had done in 78 previous Cup Matches score a century on debut. The rain-affected match was petering out to a tame draw, but nobody was leaving the ground on the second day as the dashing left-hander went past Bergon Spencer's colt record of 75 set in 1971 and closed in on triple figures. Marshall went into the last over of the match from Robert Hinds still needing seven runs for his century. Three dot balls at the start of the over only served to raise the tension and when Marshall took a single off the fourth ball, it seemed he had blown his chance. But his fellow colt, Ken Pitcher, got a single himself off the fifth ball and Marshall was back on strike for the final ball and with six runs still needed.Some things are uniquely Cup Match and collecting money for 50s and centuries is still a Cup Match tradition. Marshall made quite a lot of money that day.And even when a Royal Gazette reporter asked him about the possibility of beating Lloyd James' record 988 runs and becoming the first batsman to score 1,000 runs, Marshall seemed ready for the challenge.“Now that would really be something, wouldn't it,” was his response.Marshall's colt record was broken in 2003 when South African Saleem Mukudden scored 106 not out at Wellington Oval and then followed that up with 160 not out in Somerset, the fourth highest individual total in Cup Match. In just four innings he amazed 307 runs at an average of 153.50.Controversy continued in 1981 when bowler Ken Pitcher was dropped in favour of colt Ritchie Foggo, a batsman, in one of three changes which also saw Allen Richardson axed and Terry Fray, a reserve for Somerset in 1979, was brought into the team captained for the first time by Clarence Parfitt in place of the retired Neville Darrell.Reportedly Parfitt, one of the selectors that night, was not in favour of Foggo's inclusion and duly batted him number nine in the first innings and number 11 in the second.To this day it appears Fray's inclusion was only ever going to be a one-off as the selection for St George's meant that he could not now play for Somerset. Despite scoring 44 as an opener in the first innings and 26 in the second innings at number six, Fray was never in the frame at St George's again.Also never to play again were the two captains, Joe Bailey and Parfitt, who announced their retirement immediately after the match. Not only did Parfitt go out a loser in his last Cup Match, but he also suffered through one of his worst performances as a bowler, going for 77 runs in his 18 overs as Somerset amassed a massive 377 in the first innings.This was the year that Somerset batsman Winston Reid stood toe to toe with Parfitt and won the battle, smashing Parfitt for several boundaries including a six over square leg to bring up his 50 as he led the scoring with 82. Thirty years later Reid talked about the match he wasn't even supposed to be playing.“He was a great bowler and you can't take anything away from him, but at that particular time he was on his way out and probably a little bit past his prime,” said Reid.“That day I decided ‘Parfitt, I'm going to have some fun with you'.”Reid remembers there being a wet spot on the pitch, which St George's hoped Parfitt would exploit, but it backfired.“I didn't have a particularly good season and a lot of people were saying I shouldn't be playing, but I remember Joe Bailey saying ‘I'm not going to St George's without you'. He knew I was capable at that time of scoring runs, and so I went out there and said I'm going to have some fun.“I picked out areas on the pitch and if Parfitt pitched the ball in that area then I was going to go after him. There were a couple of times he came a bit close and I hit him. Then I walked down tapping the crease and said ‘P, pitch up the ball' and he said ‘no, no I'm not going back up there'.“You get to a stage in your life, 35, 36, 37 when the fingers aren't working as good as they used to and that's when you take advantage. I caught him at the end and took advantage because you wouldn't have been able to do it earlier. He wasn't as devastating as the Parfitt we knew. He was great bowler and good competitor and we had great fun playing together in England. In fact the whole '79 (ICC trophy) team were great friends.”1981 served as the last year that the final trial matches were played on a Thursday. In those days Somerset selected their team on the Friday night and St George's the Saturday night, but since 1982 both the last trial and team selections take place on the Saturday before Cup Match.After a draw in 1982 in Somerset, St George's finally reclaimed the trophy in 1983 as second-year captains Clevie Wade and John Tucker squared off.Wade got some key breaks in this rain-hit match after winning the toss, sending Somerset in and then dismissing them for 118, Colin Blades leading the way with 44 as Noel Gibbons and colts Roger Leverock and Stan Smith all took three wickets. Leverock, who claimed Winston Reid's wicket with his first delivery in Cup Match, had a wicket in each of his first three overs.St George's, leading by 42 runs on first innings, then dismissed Somerset for 165 in the second innings (Andre Manders 53 not out) before reaching their winning total of 124 for the loss of seven wickets. After four years the cup was going back to the East End, thanks to opener Allen Richardson's 24 not out as he lost seven partners in the 124-run chase.The '83 match also saw top commentator Tony Cozier making a guest appearance on ZBM's broadcasting team which included Randy Horton as a first time commentator and Joe Brown, making it the most listened to station that year, though Cozier almost didn't make it after the Immigration Department initially refused him a work permit!Cozier, still commentating, went to school with Colin Blades in Barbados. In a post-match interview he raved about the quality of fielding produced by Charlie Marshall who was then one of Bermuda's most exciting cover point fielders. In fact Cozier compared him to some of the world's best.The '84, '85 and '86 matches all failed to produce a win as Clevie Wade was replaced as captain after leaving the St George's league team in '85 to join Western Stars. A similar act in '78 when he joined Bailey's Bay, albeit under more controversial circumstance, caused Wade to be dropped by the East Enders, five years before he won the cup back for his home town club as captain.A new captain was now in place with Wendell Smith taking on the leadership role in '85, the match in which Wade scored his first Cup Match century in the first innings. Somerset colt, 18-year-old Richard Basden signalled his arrival on the Cup Match stage by becoming the first player to score two 50s on debut. In fact he added a third straight 50 the following year at Somerset as Arnold Manders completed his maiden Cup Match century just moments before the rain came down to end the match on the second afternoon.Three controversial decisions cast a shadow over the 1987 match which produced a win after four draws. Clay Smith made the controversial decision not to travel with the Bermuda youth team to Ireland in order to play in Cup Match. David Adams had his Cup Match hopes dashed by a suspension by the BCB a week before the final trial match.There was controversy, too, in the selection of another player following a one-year suspension. Charlie Marshall ended his suspension prior to the last trial and was selected to lead the Vice President's XI in what was his first match of the season. If nothing else Marshall knows how to produce the spectacular and he duly scored a century in the trial and left it to the selectors to ponder his selection that evening.In those days it was common for both clubs to play at least five trial matches, in fact St George's once had a policy that a new player trying to break into the team had to play in five trial matches to be eligible for selection. The St George's selectors were convinced Marshall was a gamble worth taking.For the match in Somerset, St George's were without a specialist ‘keeper with Allan Douglas coaching and Dean Minors playing for the youth team in Ireland. Anthony Trott was recalled as wicketkeeper, ending 12 long years between his first and second appearances. He took four catches behind the stumps and played on winning teams in his only two appearances.Going into the match captain Wendell Smith vowed to get his first Cup Match win and stated his intended declaration time of 3.00 if St George's batted first. He knew time was critical and he did declare at 3.30 even though Charlie Marshall was on 84 and nearing a milestone of being only the third player behind Lloyd James and Rupert Scotland to score two Cup Match centuries.In the end Smith was vindicated, as St George's were able to force the follow-on and after dismissing Somerset for 186 in the second innings, reached 72-1 to win a thrilling match by nine wickets with seven overs remaining.“I told the guys we would declare at 3.00 but we lost a couple of wickets so we put it back to 3.30,” Smith explained after the match.“I told Charlie when he was on 50 that I was giving him 45 minutes to get to his 100. He told me it really wasn't important. That shows what a team man he is.”Selection controversy continued the following year at Wellington Oval when colt Minors beat out Douglas for the wicketkeeping job, though the selectors took the easy way out and included Douglas as a batsman. At the other end Terry Burgess was dropped by Somerset as Kyle Lightbourne more known for his football exploits, made his debut as a fast bowler and played four years before becoming a professional footballer in England in 1992.The match finished in a draw as Arnold Manders took individual honours with his second century. Manders was often the ‘fall guy' at St George's as, despite finishing his career in 1999 with 688 runs, he was dropped three times by the East Enders.Cousins Charlie Marshall and Noel Gibbons each had two ducks in 1988. Both were dismissed first ball in the first innings and, with a draw inevitable, also failed to score in the second innings. Same result again in '89 as Somerset colt Anthony Amory led the batting with a game-high 69 in the first innings of the drawn match.St George's did win again in 1991 when Andre Manders became the first captain to declare in the third innings in Cup Match and lose, though Somerset were the challengers not the champions. Chasing victory, Manders declared at 3.30 on the second day, giving St George's 110 minutes and 20 overs to score 205, which they achieved with the loss of three wickets.Smith brothers Wendell and Clay stole the show in 1992 as records tumbled with both players scoring centuries as Wendell went past Lloyd James 988 to become the highest scorer in Cup Match. The 129 was Wendell's first century, finally making up for his 96 in 1988 when he was caught on the square leg boundary going for a six off Dexter Basden.Clevie Wade was dropped for a second time by St George's in 1993 as Wendell ruled himself out and Graham Fox took over the captaincy for the first time. Victory came again for St George's in 1994 as veteran Noel Gibbons was dropped for the first time, having been left out of the final trial match for failing to pay his dues. It signalled the end of his Cup Match career at 38 and while he finished high up in the batting aggregate with 783 runs the man who was one of Bermuda's finest batsmen for two decades never did score a century in Cup Match, finishing with a best knock of 82.Nonetheless, St George's did win the '94 match under Graham Fox by six wickets. This time they were set 237 to win in 65 minutes plus 20 overs and took up the challenge.A significant change came about in 1995 when the year-about was introduced in Cup Match. Prior, the match would stay two years at a venue if the visiting team did not win in the first year, something which sometimes encouraged defensive cricket on the part of the home team. It was also the year Wendell Smith returned after a two-year absence to score the seven runs he needed to become the first batsman to reach 1,000 runs in Cup Match. A year later an extra hour was introduced in a bid to produce more results as Clay Smith took over from Graham Fox and duly lost at Somerset in 1996 after the West Enders clinched a thrilling three wicket win after being set 252 to win in 76 minutes plus the mandatory 20 overs. Clarkie Trott's overthrow for four with two balls remaining sealed the win for Somerset.Treadwell Gibbons became the oldest colt in Cup Match history at age 39 when he was selected for Somerset 20 years after first trying out as a wicketkeeper in St George's. Gibbons scored a valuable 60 in an opening stand of 119 with Albert Steede scoring 108 to go with the 71 he scored in the first innings.Clay Smith did redeem himself the following year in St George's when the home team won by eight wickets following knocks of 79 and 90 not out from Glenn Blakeney.Back at Somerset, Mark (Beaver) Ray scored 103 not out to help St George's achieve a draw after recovering from 118-6 to post 225-9 declared.“I'll never play for you again”, was the promise from Clay Smith in 1999 when, after leaving St George's to take a player-coach job with neighbours St David's, he was dropped by the champions during a tense selection night.Obviously Smith did play again for St George's two years later and went on to surpass 1,000 runs before retiring in 2008. Janeiro Tucker (the only other player beside Clay to score three Cup Match centuries) became the first Somerset player to reach triple figures at Wellington Oval as the visitors saved themselves from sure defeat by batting for six and a half hours on the second day.Two years later at Wellington Oval he was back at it, stroking the highest Cup Match score by any batsman when he blasted 186 from 142 balls off 18 fours and 13 sixes before admitting fatigue led to his demise as he neared the elusive 200.“When I got to 150 I was pretty sure I could get it because the bowling was that tight,” said Tucker after the match.“But I started to tire around 150 and told Richard (Basden) to try and take a little bit of the strike away so I could catch myself.”Two years ago Tucker stroked a third century at Wellington Oval (126 not out) while Lionel Cann hit a maiden century for St George's to secure a draw.Tucker (1231) is just 126 runs behind the now-retired Charlie Marshall (1357) as the leading all-time run-getter. With his record at Wellington Oval few would bet against him doing something spectacular again this year.