The OCCC first entered an old boys’ tournament in 1990, reaching the semi-finals of the Cricket World Trophy. In the next four seasons we struggled to make any impression, withdrawing in 1995. We gained entry to the Brewers Cup in 2001, winning the competition in 2002, 2004 and 2006 and being losing finalists in 2005. In 2007 we were invited into the Cricketer Cup, and in the same season we also entered the Cricket World Trophy, winning that competition. In 2008 and 2013 we reached the final of the Cricketer Cup, winning it at the third time of trying in 2014 when he beat Bradfield. We reached the final for the fourth time in 2016, and secured our second win in 2018 when we won a 20-over contest against Malvern.
All records as at the end of 2021
All records relate to the Cricketer Cup
| P | W | L | Years | |
| Cricketer Cup | 39 | 28 | 11 | 2007-20 |
| Brewers Cup | 18 | 15 | 3 | 2001-06 |
| Cricket World Trophy | 14 | 6 | 8 | 1990-94, 2003, 2007-08 |
Batting – Most runs
| M | I | NO | HS | Runs | Av | 50 | 100 | |
| SR Waters | 32 | 32 | 2 | 103 | 1141 | 38.03 | 7 | 2 |
| AC Cope | 31 | 28 | 6 | 133 | 914 | 41.55 | 5 | 1 |
| JAL Scriven | 25 | 23 | 2 | 176 | 866 | 41.24 | 3 | 3 |
| MJ Crump | 34 | 28 | 4 | 107* | 715 | 29.79 | 4 | 1 |
| TJ Crump | 27 | 25 | 6 | 65 | 639 | 33.63 | 4 | – |
| BRM Scriven | 13 | 13 | 2 | 82 | 556 | 50.55 | 4 | – |
| B Broughton | 20 | 17 | 3 | 116 | 381 | 27.21 | – | 1 |
Batting – Hundreds
| Date | Runs | Name | Opposition | Minutes | |
| 2019 | 102 | JAL Scriven | Old Alleynians | 46 | |
| 2018 | 100 | JAL Scriven | Eton Ramblers | – | |
| 2015 | 133 | AC Cope | O Tonbridgians | 95 | |
| 2014 | 100 | * | SR Waters | O Carthusians | 163 |
| 2014 | 176 | JAL Scriven | OMTs | – | |
| 2009 | 103 | * | SR Waters | Haileybury Hermits | 98 |
| 2008 | 107 | * | MJ Crump | O Cliftonians | – |
Bowling – Most Wickets
| O | M | R | W | Av | Econ | BB | |
| SR Waters | 255.2 | 22 | 1048 | 56 | 18.71 | 4.11 | 7-32 |
| MJ Crump | 156.0 | 12 | 616 | 30 | 20.53 | 3.95 | 6-7 |
| JAL Scriven | 192.0 | 17 | 732 | 38 | 19.26 | 3.81 | 4-34 |
| W Rollings | 167.2 | 17 | 657 | 30 | 21.90 | 3.94 | 4-39 |
| HC Watkinson | 98.0 | 9 | 446 | 26 | 17.15 | 4.55 | 4-14 |
Best Bowling
| O | M | R | W | |||
| SR Waters | 10 | 1 | 32 | 7 | O Etonians | 2015 |
| MJ Crump | 7 | 3 | 7 | 6 | Shrewsbury | 2013 |
| N Thorpe | 7.4 | 3 | 10 | 5 | Haileybury | 2018 |
| GCW Webb | 10 | 1 | 25 | 5 | O Malvernians | 2010 |
Most Appearances
| No | Seasons | |
| MJ Crump | 34 | 2007-2018 |
| SR Waters | 32 | 2007-2019 |
| AC Cope | 31 | 2007-2019 |
| T Crump | 27 | 2007-2017 |
Other records
Highest total – 332 for 4 v OMTs, 1st round (2014)
Lowest total – 152 v Old Malvernians, final (2008)
Highest total against – 301 for 7 v Old Tonbridgians, 1st round (2015)
Lowest total against – 33 v Shrewsbury, Cricketer Cup semi-final (2013)
Largest margin of victory – 252 runs v OMTs, 1st round (2014)
Largest margin of defeat