Your returns are stopping the loop in the first iteration. Look at using `continue;` instead.

you also need to move the second foreach out of the first because the list of players is not generated yet.
Dont forget to add null checks for findPlayer as it could be null

        void GetTopBarrels(BasePlayer player)
        {
            StringBuilder result = new StringBuilder("Top Player Barrels Hit\n\n");
            Dictionary<BasePlayer, float> TopBarrels = new Dictionary<BasePlayer, float>();

            //What I want: For every player which is in cached player stats, do the following
            //What ACTUALLY happens: It only picks one player (the same one every time) out of the cached player stats and not a list of 5
            foreach (KeyValuePair<ulong, PLRStats> individualStats in cachedPlayerStats)
            {
                Puts(individualStats.Value.PlayerID.ToString());
                int barrels = individualStats.Value.BarrelsHit;
                if (barrels > 0)
                {
                    Puts("Barrels Hit over 0");
                    BasePlayer findPlayer = BasePlayer.FindByID(individualStats.Value.PlayerID);

                    if (!TopBarrels.ContainsKey(findPlayer))
                    {
                        TopBarrels.Add(findPlayer, barrels);
                        Puts("Adding player to the top Barrels list");
                    }
                }
            }

            if (TopBarrels.Count > 0)
            {
                foreach (KeyValuePair<BasePlayer, float> topFivePlayer in TopBarrels.OrderByDescending(x => x.Value).Take(5))
                {
                    Puts("Getting all the top players");
                    PLRStats.TryLoad(topFivePlayer.Key.userID);

                    result.Append($" {topFivePlayer.Key.displayName} with {TopBarrels[findPlayer]} Barrels Hit");
                }
                SendMessage(player, result.ToString());
                Puts("Sent Message");
            }
            else
            {
                SendMessage(player, "Nobody on the server has top amount of Barrels Hit!");
                return;
            }
        }​