If you don't review I'll set Nargles on you.
Maybe when he was younger he would have seen the Quidditch Cup. Maybe he would have seen himself, captain of the greatest team Hogwarts had ever seen lifted onto the shoulders of his beaters, Fred and George Weasley and holding the cup above his head for the throngs of screaming Gryffindors to see. Maybe he would have seen himself being drafted by Mold Mngwas, the Minister shaking his hand as he lead England to victory in the World Cup. Maybe he would have seen himself rolling in a pile of galleons and sickles, his parents beaming in the background. But no more. Those were a child's wants. A boys dreams.
He came from a wonderful background. A happy family, dedicated to each other, loving. He had everything as a child, but he had dreams of glory that could not be quashed. He was a man with a plan, dedicated to the point of obsession and ambitious to boot. He had always known what he wanted and how to make that happen. When his letter to Hogwarts had come, he had been excited beyond belief, not because he was going to the school so much as the realization of his plans.
In school he was dedicated, like he was in every aspect of his life. He wasn't a particularly gifted wizard, but he worked, though even he had to admit, not had hard as he worked at Quidditch. Quidditch. He loved it. He loved to fly, he loved the wind in his hair, the companionship it offered and he loved the sport itself. But nothing compared to the thrill of competition. He wanted to win at everything, and Quidditch was a channel for that desire.
Yes, maybe at Hogwarts, when the possibility of victory and the need for recognition still thrummed though his veins, that was what he would have seen. A silly cup in recognition of winning a silly game. It was funny that he, who had so much of everything important, could have wanted so much of everything unimportant.
There had been a time in his life, a dark time, when he would have seen his family in that mirror. His mother, his father, his sister, her husband. Yes, he had no doubt he would have seen them. While he had been off living his dreams, their lives had ended for no reason then the dictation of someone's whim. It hadn't been his fault, he realized that now, but it had seemed like it was at the time. Even now, the dull cold pit in his stomach still followed him wherever he went. However, their faces no longer haunted him, their voices no longer echoed in the deep confines of his mind. He had come to peace with their loss, and now, only happiness accompanied their memories. He would not allow grief and guilt to tarnish them.
When darkness had truly fallen across England, and Voldamort had seemed invincible, he didn't know what he would have seen. What does peace and light and good and innocence look like? Because that had been all he had wanted for what seemed like the longest time.
But that too had come to pass and now he stood, old and grey, the best years of his life behind him according to some, the best to come according to others. His shoulders were stooped; he needed a cane to walk. His eye sight was poor, his hearing worse, and he had hair in all the wrong places. His life had not followed his plan. He was never more then a back up Keeper of Puddlemere United, he had never met the Minister of Magic. He had not married a model, but a chubby muggle girl who loved him. He had slaved away at a dead end job in the Department of Magical Games and Sports for fifty seven years, and his family had never had much money. He had three daughters who loved Quidditch and one son who hated it.
His life had not been easy, in fact, it had been quite difficult. But he wouldn't have traded a moment of it for the "glory days". Yes at eighty nine Oliver Wood stood before the Mirror of Erised and saw just himself looking back at him. Completely content.