| Awards |
 | Year #37: ⌘ Playboy was a member of team Full Stride Eventers, #2 team in yearly points overall. |
| Year #37: ⌘ Playboy was a member of team Full Stride Eventers, #3 team in total points overall. |
 | Year #37: ⌘ Playboy was #9 horse in most points overall. |
| Year #37: ⌘ Playboy was #5 horse in most winnings overall. |
| Year #36: ⌘ Playboy was a member of team Full Stride Eventers, #3 team in total points overall. |
| Year #36: ⌘ Playboy was #4 horse in most winnings overall. |
| Year #36: ⌘ Playboy was #12 horse in most points overall. |
| Year #36: ⌘ Playboy was a member of team Full Stride Eventers, #10 team in yearly points overall. |
| Year #35: ⌘ Playboy was a member of team Full Stride Eventers, #3 team in yearly points overall. |
| Year #35: ⌘ Playboy was #4 horse in most winnings overall. |
| Year #35: ⌘ Playboy was #17 horse in most points overall. |
| Year #35: ⌘ Playboy was a member of team Full Stride Eventers, #3 team in total points overall. |
| Year #34: ⌘ Playboy was #24 horse in most points overall. |
| Year #34: ⌘ Playboy was a member of team Full Stride Eventers, #4 team in total points overall. |
| Year #34: ⌘ Playboy was a member of team Full Stride Eventers, #5 team in yearly points overall. |
| Year #34: ⌘ Playboy was #3 horse in most winnings overall. |
 | Year #33: ⌘ Playboy placed #3 in the HEWG Team Competition - Eventing. |
| Year #33: ⌘ Playboy was a member of team Full Stride Eventers, #8 team in yearly points overall. |
| Year #33: ⌘ Playboy was a member of team Full Stride Eventers, #4 team in total points overall. |
| Year #32: ⌘ Playboy was a member of team Full Stride Eventers, #6 team in total points overall. |
| Year #32: ⌘ Playboy placed #2 in the HEWG Team Competition - Eventing. |
| Year #32: ⌘ Playboy was a member of team Full Stride Eventers, #5 team in yearly points overall. |
| Year #31: ⌘ Playboy was a member of team Full Stride Eventers, #22 team in yearly points overall. |
| Year #31: ⌘ Playboy was a member of team Full Stride Eventers, #6 team in total points overall. |
| Year #30: ⌘ Playboy was #13 horse in most yearly winnings. |
| Year #30: ⌘ Playboy was #6 Eventing horse in most yearly winnings. |
| Year #30: ⌘ Playboy was #23 horse in most yearly points. |
| Year #30: ⌘ Playboy was a member of team Full Stride Eventers, #6 team in total points overall. |
| Year #30: ⌘ Playboy was a member of team Full Stride Eventers, #6 team in yearly points overall. |
| Year #29: ⌘ Playboy was #2 Eventing horse in most yearly winnings. |
| Year #29: ⌘ Playboy was #8 horse in most yearly points. |
| Year #29: ⌘ Playboy was a member of team Full Stride Eventers, #2 team in yearly points overall. |
| Year #29: ⌘ Playboy was a member of team Full Stride Eventers, #8 team in total points overall. |
| Year #29: ⌘ Playboy was #2 horse in most yearly winnings. |
| Year #28: ⌘ Playboy was a member of team Full Stride Eventers, #14 team in total points overall. |
| Year #27: ⌘ Playboy was a member of team Full Stride Eventers, #14 team in total points overall. |
| Year #27: ⌘ Playboy was #4 horse in most yearly winnings. |
| Year #27: ⌘ Playboy was #1 Eventing horse in most yearly winnings. |
 | Year #27: Jenny Jenkins - ⌘ Playboy finished #5 in HEEF Level 6: Intermediate Novice. |
 | Year #25: Sean Fox-Pitt - ⌘ Playboy finished #14 in HEJRA Level 5: Preliminary. |
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Breezy and Pleasant
