The 55th Alumni race was held on Wimbledon Common on December 13th 2008.
2008 Individual Results
| 1 | 26:05 | James | McMullan | Charterhouse | |
| 2 | 26:29 | Simon | Wurr | Warwick | |
| 3 | 27:50 | Ed | Knudsen | Sherborne | |
| 4 | 28:11 | Charles | Sykes | Sedbergh | |
| 5 | 28:51 | Francis | Blunt | Sedbergh | |
| 6 | 29:04 | Joe | Symonds | Sedbergh | |
| 7 | 29:33 | David | Symons | Bournemouth | M40 |
| 8 | 29:40 | Andrew | Lawrence | Sedbergh Guest | |
| 9 | 29:48 | Chris | Finill | Harrow County | M40 |
| 10 | 30:09 | Simon | Barnby | Sedbergh | |
| 11 | 30:13 | Patrick | Wooddisse | Denstone | |
| 12 | 30:20 | Miles | Copeland | Westminster | |
| 13 | 30:24 | Neil | Riley | St George's Weybridge | M40 |
| 14 | 30:31 | Sam | Stell | Sedbergh | |
| 15 | 30:58 | Robert | Rigby | Ampleforth | M40 |
| 16 | 31:10 | Geoff | Watson | Sedbergh | |
| 17 | 31:15 | Anthony | Doolittle | Winchester | |
| 18 | 31:18 | Charlie | Hammon | Oundle | |
| 19 | 31:19 | John | Shaw | Winchester | M40 |
| 20 | 31:20 | Mark | Wainwright | Westminster | |
| 21 | 31:21 | Mark | Cranwell | Harrow County | |
| 22 | 31:22 | Jonathan | Potts | Oundle | |
| 23 | 31:30 | Ed | Pitt-Ford | Sherborne | |
| 24 | 31:31 | Hugh | Knudsen | Sherborne | |
| 25 | 31:33 | Richard | Pitt | Charterhouse | M50 |
| 26 | 31:58 | Jerry | Watson | Dulwich | M40 |
| 27 | 32:06 | Jonathan | Barron | Winchester | |
| 28 | 32:27 | Ralph | Wooddisse | Denstone | |
| 29 | 32:33 | Richard | Evans | Westminster Guest | |
| 30 | 32:50 | Simon | Dawson | Sherborne | |
| 31 | 33:04 | Doug | Teesdale | Winchester | M40 |
| 32 | 33:23 | Oliver | Brodrick-Ward | Ampleforth | |
| 33 | 33:26 | Dan | Pescod | Dulwich | |
| 34 | 33:35 | Rameez | Khan | Westminster | |
| 35 | 33:38 | Graham | Ball | Westminster | M50 |
| 36 | 33:41 | Richard | O'Hara | Westminster | M40 |
| 37 | 34:00 | Anthony | Arthur | Ampleforth | |
| 38 | 34:16 | Charles | Farrar-Bell | Harrow | |
| 39 | 34:20 | Alex | Bangert | Oundle | |
| 40 | 34:24 | David | McKee | Westminster | |
| 41 | 34:40 | Phil | Hobbs | Sedbergh | M40 |
| 42 | 34:53 | Rhodri | Davies | Winchester | M50 |
| 43 | 34:55 | Hugh | Scorgie | Winchester Guest | M40 |
| 44 | 35:00 | Tim | Powell-Jackson | Winchester | |
| 45 | 35:03 | Rory | Henderson | Ampleforth | |
| 46 | 35:19 | John | Pocock | Sherborne | M40 |
| 47 | 35:27 | Chris | Hutber | Stowe | |
| 48 | 35:31 | Peter | Harris | Denstone | M50 |
| 49 | 35:41 | Hugh | Symonds | Sedbergh Guest | M50 |
| 50 | 36:03 | Charlie | Whitcombe | Sherborne | |
| 51 | 36:04 | Peter | Giles | Bournemouth | M50 |
| 52 | 36:31 | Max | Hobbs | Sherborne | |
| 53 | 36:41 | Peter | Bunn | Winchester | M50 |
| 54 | 36:49 | Edward | Banyard-Smith | Oundle | |
| 55 | 37:15 | Tom | Dillon | Sherborne | |
| 56 | 37:30 | Jon | Salmon | Bradfield | M40 |
| 57 | 37:41 | Toby | Vanhegan | Westminster | |
| 58 | 37:47 | Richard | Clarke | Charterhouse | M40 |
| 59 | 37:49 | Charles | Stevenson | Westminster | |
| 60 | 38:06 | Jon | Hughes | Ampleforth | |
| 61 | 38:21 | Martin | Winter | Charterhouse | M50 |
| 62 | 38:44 | Richard | Barrington | Denstone | M50 |
| 63 | 40:56 | Gareth | Bartley | Winchester | M50 |
| 64 | 41:42 | Norman | Berry | Sedbergh | M50 |
| 65 | 41:47 | Francis | Uhlman | Westminster | M50 |
| 66 | 41:56 | Gerald Ignatius | Shea | St George's Weybridge | M40 |
| 67 | 42:05 | Tony | Henderson | Bradfield | M40 |
| 68 | 42:28 | Jim | Forrest | Westminster | M50 |
| 69 | 42:32 | Charles | Pinder | Winchester | M50 |
| 70 | 42:35 | Michael | Bostelmann | Bradfield | M50 |
| 71 | 42:53 | Charles | Mason | Winchester | M50 |
| 72 | 43:37 | David | Barrington | Denstone | M50 |
| 73 | 43:53 | Neil | Harvey | Stowe | M40 |
| 74 | 44:01 | Hugh | Peltor | Denstone | M50 |
| 75 | 44:27 | Angus | Cater | Sherborne | M50 |
| 76 | 45:29 | Chris | Vernon | Dulwich | M50 |
| 77 | 45:52 | Simon | Berry | Sedbergh | M50 |
| 78 | 46:42 | Andrew | Simon | Winchester | M50 |
| 79 | 47:24 | David | Jenkins | Winchester | M50 |
| 80 | 47:46 | David | Anderson | Winchester | M50 |
| 81 | 52:48 | Finn | Teesdale | Winchester - Guest | |
| 82 | 55:45 | Richard | Weston | Stowe | M50 |
| 83 | 57:28 | Marc | Hope | Stowe | M40 |
| 84 | 1:01:15 | Bobby | Mill | Winchester | M50 |
| 85 | 1:03:38 | Ian | Teesdale | Winchester | M50 |
| DNF | | | Peltor | Ed | Marlborough |
2008 Team Results
| The King Henry VIII School Old Boys Trophy |
| 1 | Sedbergh | 24 |
| 2 | Sherborne | 76 |
| 3 | Winchester | 89 |
| 4 | Westminster | 95 |
| 5 | Ampleforth | 121 |
| 6 | Oundle | 125 |
| 7 | Charterhouse | 136 |
| 8 | Denstone | 140 |
| 9 | Harrow County | 190 |
| 10 | Dulwich | 209 |
| 11 | Bournemouth | 216 |
| 12 | St George's Weybridge | 236 |
| 13 | Warwick | 245 |
| 14 | Bradfield | 262 |
| 15 | Stowe | 268 |
| The Old Brentwood's Trophy for Veterans +40 |
| 1 | Winchester | 25 |
| 2 | Westminster | 42 |
| 3 | Charterhouse | 47 |
| 4 | Sedbergh | 67 |
| 5 | Bournemouth | 58 |
| 6 | Denstone | 68 |
| 7 | St George's Weybridge | 69 |
| 8 | Dulwich | 82 |
| 9= | Bradfield | 86 |
| 9= | Harrow County | 84 |
| 11= | Ampleforth | 92 |
| 11= | Sherborne | 92 |
| 13 | Stowe | 113 |
| The Chataway Cup for Veterans +50 |
| 1 | Winchester | 18 |
| 2 | Westminster | 25 |
| 3 | Denstone | 28 |
| 4= | Charterhouse | 35 |
| 4= | Sedbergh | 57 |
| 6 | Bournemouth | 59 |
| 7 | Bradfield | 68 |
| 8 | Sherborne | 72 |
| 9 | Dulwich | 73 |
| 10 | Stowe | 78 |