| Awards |
 | Year #21: ♚ Playboy was a member of team Cross This Country!, #9 team in yearly points overall. |
| Year #21: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
 | Year #21: ♚ Playboy was #8 horse in most points overall. |
| Year #21: ♚ Playboy was #19 horse in most winnings overall. |
| Year #20: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #20: ♚ Playboy was #4 horse in most points overall. |
| Year #20: ♚ Playboy was #14 horse in most winnings overall. |
| Year #19: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #19: ♚ Playboy was #7 horse in most winnings overall. |
| Year #19: ♚ Playboy was #3 horse in most points overall. |
| Year #18: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #18: ♚ Playboy was #7 horse in most winnings overall. |
| Year #18: ♚ Playboy was #4 horse in most points overall. |
| Year #17: ♚ Playboy was a member of team Cross This Country!, #23 team in yearly points overall. |
| Year #17: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #17: ♚ Playboy was #24 horse in most yearly winnings. |
| Year #17: ♚ Playboy was #4 horse in most points overall. |
| Year #17: ♚ Playboy was #6 horse in most winnings overall. |
| Year #17: ♚ Playboy was #7 Dressage horse in most yearly winnings. |
| Year #16: ♚ Playboy was #5 horse in most points overall. |
| Year #16: ♚ Playboy was #8 horse in most winnings overall. |
| Year #16: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #16: ♚ Playboy was a member of team Cross This Country!, #10 team in yearly points overall. |
| Year #15: ♚ Playboy was #7 horse in most winnings overall. |
| Year #15: ♚ Playboy was #6 horse in most points overall. |
| Year #15: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #15: ♚ Playboy was a member of team Cross This Country!, #24 team in yearly points overall. |
| Year #14: ♚ Playboy was #3 horse in most winnings overall. |
| Year #14: ♚ Playboy was #4 horse in most points overall. |
| Year #14: ♚ Playboy was #10 Jumper horse in most yearly winnings. |
| Year #14: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #14: ♚ Playboy was a member of team Cross This Country!, #2 team in yearly points overall. |
 | Year #14: Dimitris - ♚ Playboy finished #8 in HEJF Level 8: Grand Prix. |
 | Year #14: ♚ Playboy finished #1 in HEJF Level 8: Grand Prix Championship Show. |
 | Year #14: ♚ Playboy placed #1 in the HEWG Team Competition - Jumping. |
| Year #13: ♚ Playboy was #3 horse in most winnings overall. |
| Year #13: ♚ Playboy was #6 horse in most points overall. |
| Year #13: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #13: ♚ Playboy placed #3 in the HEWG Team Competition - Jumping. |
| Year #12: ♚ Playboy was #4 horse in most winnings overall. |
| Year #12: ♚ Playboy was #4 horse in most points overall. |
| Year #12: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #12: ♚ Playboy was a member of team Cross This Country!, #1 team in yearly points overall. |
| Year #12: ♚ Playboy placed #2 in the HEWG Team Competition - Jumping. |
| Year #11: ♚ Playboy was #3 horse in most winnings overall. |
| Year #11: ♚ Playboy was #2 horse in most points overall. |
| Year #11: ♚ Playboy was #16 Jumper horse in most yearly winnings. |
| Year #11: ♚ Playboy was a member of team Cross This Country!, #1 team in total points overall. |
| Year #11: ♚ Playboy was a member of team Cross This Country!, #2 team in yearly points overall. |
| Year #11: Dimitris - ♚ Playboy finished #3 in HEJF Level 7: Advanced. |
| Year #11: ♚ Playboy finished #10 in HEJF Level 7: Advanced Championship Show. |
| Year #10: Playboy placed #1 in the HEWG Individual Competition - Cross Country. |
| Year #10: Playboy placed #1 in the HEWG Team Competition - Cross Country. |
| Year #10: Playboy finished #3 in HECCF Level 9: International Championship Show. |
| Year #10: Stella M - Playboy finished #1 in HECCF Level 9: International. |
| Year #10: Playboy was a member of team Cross This Country!, #1 team in yearly points overall. |
| Year #10: Playboy was a member of team Cross This Country!, #2 team in total points overall. |
| Year #10: Playboy was #1 horse in most yearly points. |
| Year #10: Playboy was #1 Cross Country horse in most yearly winnings. |
| Year #10: Playboy was #1 horse in most yearly winnings. |
| Year #10: Playboy was #3 horse in most points overall. |
| Year #10: Playboy was #3 horse in most winnings overall. |
| Year #9: Playboy was #5 Cross Country horse in most yearly winnings. |
| Year #9: Playboy was #14 horse in most yearly winnings. |
| Year #9: Playboy was #4 horse in most points overall. |
| Year #9: Playboy was #16 horse in most winnings overall. |
| Year #9: Playboy was a member of team Cross This Country!, #2 team in total points overall. |
| Year #9: Playboy was a member of team Cross This Country!, #6 team in yearly points overall. |
| Year #9: Hugh - Playboy finished #3 in HECCF Level 8: Advanced. |
| Year #9: Hugh - Playboy finished #5 in HECCF Level 9: International. |
| Year #9: Playboy finished #1 in HECCF Level 8: Advanced Championship Show. |
| Year #9: Playboy finished #8 in HECCF Level 9: International Championship Show. |
| Year #9: Playboy placed #1 in the HEWG Team Competition - Cross Country. |
| Year #8: Playboy was #18 horse in most winnings overall. |
| Year #8: Playboy was #4 horse in most points overall. |
| Year #8: Playboy was #18 Cross Country horse in most yearly winnings. |
| Year #8: Playboy was a member of team Cross This Country!, #3 team in total points overall. |
| Year #8: Playboy was a member of team Cross This Country!, #23 team in yearly points overall. |
| Year #8: Hugh - Playboy finished #3 in HECCF Level 8: Advanced. |
| Year #8: Playboy finished #4 in HECCF Level 8: Advanced Championship Show. |
| Year #8: Playboy placed #1 in the HEWG Team Competition - Cross Country. |
| Year #8: Playboy placed #2 in the HEWG Individual Competition - Cross Country. |
| Year #7: Playboy was a member of team Cross This Country!, #3 team in total points overall. |
| Year #7: Playboy was #10 horse in most winnings overall. |
| Year #7: Playboy was #5 horse in most points overall. |
| Year #7: Playboy was #6 horse in most yearly winnings. |
| Year #7: Playboy was #2 Cross Country horse in most yearly winnings. |
| Year #7: Hugh - Playboy finished #7 in HECCF Level 7: Intermediate. |
| Year #7: Hugh - Playboy finished #6 in HECCF Level 7: Intermediate. |
| Year #6: Playboy was #18 horse in most winnings overall. |
| Year #6: Playboy was #10 horse in most points overall. |
| Year #6: Playboy was #5 Cross Country horse in most yearly winnings. |
| Year #6: Hugh - Playboy finished #4 in HECCF Level 6: Intermediate Novice. |
| Year #6: Hugh - Playboy finished #5 in HECCF Level 7: Intermediate. |
| Year #6: Playboy finished #2 in HECCF Level 6: Intermediate Novice Championship Show. |
| Year #6: Playboy finished #7 in HECCF Level 7: Intermediate Championship Show. |
 | Year #6: Hugh - Playboy finished #14 in HEJRA Level 4: Training. |
| Year #6: Hugh - Playboy finished #1 in HEJRA Level 5: Preliminary. |
| Year #5: Stanley - Playboy finished #10 in HECCF Level 6: Intermediate Novice. |
| Year #5: Playboy was #13 horse in most winnings overall. |
| Year #5: Playboy was #13 horse in most points overall. |
| Year #5: Playboy was #21 horse in most yearly winnings. |
| Year #5: Playboy was #6 Cross Country horse in most yearly winnings. |
| Year #5: Hugh - Playboy finished #5 in HEJRA Level 4: Training. |
| Year #4: Playboy was #2 Cross Country horse in most yearly winnings. |
 | Year #4: Playboy was #8 top cross country sire overall. |
| Year #4: Playboy was #6 top eventing sport horse sire. |
| Year #4: Playboy was #6 top dressage sport horse sire. |
| Year #4: Playboy was #8 top jumping sport horse sire. |
| Year #4: Playboy was #1 top cross country sport horse sire. |
| Year #4: Playboy was #3 horse in most yearly winnings. |
| Year #4: Playboy finished #9 in HECCF Level 5: Preliminary Championship Show. |
| Year #4: Playboy finished #1 in HEEF Level 4: Training Championship Show. |
|
|
Morning Snow followed by Sunshine
